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Here is a chemical reaction formula: Reactants are:m1_m4:OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C;m2:[H-].[Na+];m3:C1(=CC=CC=C1)C.CC(=O)C, Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:C(#C)C=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine (495 mg, 1.5 mmol) was dissolved in toluene (30 mL) and catalytic sodium hydride (10 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture was removed by distillation. The mixture was cooled to 25° C. and water (20 mL) and ethyl acetate (40 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×40 mL) and the combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate:hexane (1:3) as eluant to afford 5-ethynyl-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine as an oil (250 mg, 61%). LRMS (EI) m/e 217 (M+ +H --isobutylene), 216 (M+ --isobutylene); 1H NMR (CDCl3, 300 MHz): δ 8.59 (b-s, 1H), 8.42 (d, J=1.5 Hz, 1H), 7.59 (b-s, 1H), 4.94 (b-m, 0.5H), 4.77 (b-m, 0.5H), 3.64 (b-m, 2H), 3.21 (s, 1H), 2.39 (m, 1H), 1.75-2.0 (b-m, 3H), 1.46 (s, 3H), 1.21 (s, 6H). |
Here is a chemical reaction formula: Reactants are:m2:[H-].[Na+];m1_m4:OC(CC=1C=C(C=NC1)C1CCC(N1C)=O)(C#C)C;m3:C1(=CC=CC=C1)C.CC(=O)C, Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:C(#C)C=1C=C(C=NC1)C1CCC(N1C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine (200 mg, 0.77 mmol) was dissolved in toluene (20 mL) and catalytic sodium hydride (5 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture were removed by distillation. The mixture was cooled to 25° C. and water (10 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate as eluant to afford 5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine as a solid (125 mg, 81%). M.p. 83°-84° C.; 1H NMR (CDCl3, 300 MHz): δ 8.69 (d, J=2 Hz, 1H), 8.46 (d, J=2 Hz, 1H), 7.62 (t, J=2 Hz, 1H), 4.57 (dd, J=7, 6 Hz, 1H), 3.28 (s, 1H), 2.70 (s, 3H), 2.45-2.65 (m, 3H), 1.88 (m, 1H). |
Here is a chemical reaction formula: Reactants are:m3_m4_m6:BrC=1C=C(C=NC1)N1C=CCC1;m3_m4_m6:C(=O)(OCC1=CC=CC=C1)N1[C@H](C(=O)O)CCC1;m1_m5:C(=O)(OCC1=CC=CC=C1)N1[C@H](C(=O)O)CCC1;m2:[BH4-].[Na+], Reagents are:m3_m4_m6:C(Cl)Cl;m1_m5:COCCOC, and Products are 0:BrC=1C=C(C=NC1)C1NCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Carbobenzyloxy-L-proline (37.4 g, 150 mmol) was dissolved in DME (100 mL) and cooled to 0° C. with stirring. Sodium borohydride (1.89 g, 50 mmol) was added in portions (gas evolution) and the resulting mixture was stirred for 2 h at 25° C. affording a colorless solution. The solvents were removed in vacuo and the resuting gum dissolved in methylene chloride (50 mL). To this solution was added a mixture of 5-bromo-3-(2-pyrrolin-1-yl)pyridine (5.63 g, 25 mmol) and carbobenzyloxy-L-proline (6.23 g, 25 mmol) in methylene chloride (50 mL) and this was stirred at 25° C. for 36 h. The solvent was removed in vacuo and 6M HCl (200 mL) was added to the residue. The resulting solution was extracted with isopropyl acetate (200 mL) and the phases separated. The acidic aqueous phase was basified with solid NaOH to pH 14 and then extracted with methylene chloride (3×200 mL). The combined methylene chloride extracts were washed with brine (150 mL), dried (MgSO4) and concentrated in vacuo. The crude product was chromatographed on silica gel with ethyl acetate, then methanol:ethyl acetate (1:19 to 1:9) as eluants to afford 5-bromo-3-(2-pyrrolidinyl)pyridine (4.1 g, 72%) obtained as a pale yellow oil. LRMS (EI) m/e 227 (C9H11N281 Br--H+) 225 (C9H11N279Br--H+); 1H NMR (DMSO-d6, 300 MHz) δ 8.53 (d, J=2.2 Hz, 1H), 8.49 (d, J=1.8 Hz, 1H), 7.91 (t, J=2.0 Hz, 1H), 4.17 (t, J=7.7 Hz, 1H), 3.18 (m, 1H), 3.06 (m, 1H), 2.00 (m, 1H), 2.07 (s, 1H), 2.00-1.77 (m, 2H), 1.63 (m, 1H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrC=1C=C(C=NC1)C1NCCC1;m1_m2_m3:C(=O)O, Reagents are:m1_m2_m3:C=O, and Products are 0:BrC=1C=C(C=NC1)C1N(CCC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Enantiomerically enriched 5-bromo-3-(2-pyrrolidinyl)pyridine (1.82 g, 8 mmol) was dissolved in a mixture of 98% formic acid (16 mL) and 37% aqueous formaldehyde (8 mL). The solution was heated with stirring for 3 h at 80° C. After cooling to 25° C. the mixture was concentrated in vacuo and water (30 mL) added. The mixture was basified with solid NaOH to pH 12 and extracted with methylene chloride (3×40 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude material was chromatographed on silica gel with ethyl acetate:hexane (1:3 ) as eluant to afford 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine as an oil, 1.63 g,84%. LRMS (EI) m/e 242 (C10H13N281Br), 241 (C10H13N279Br--+H), 240 (C10H11 N279Br), 239 (C10H13N279Br--+H); 1H NMR (DMSO-d6, 300 MHz) δ 8.55 (d, J=2.1 Hz, 1H), 8.44 (d, J=1.9 Hz, 1H), 7.88 (t, J=1.9 Hz, 1H), 3.24 (b-dt, J=8.1 Hz, 1H), 3.10 (t, J=8.0 Hz, 1H), 2.36 (m, 1H), 2.1s (s, 3H), 1.95 (m, 1H), 1.85 (m, 1H), 1.70 (m, 1H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(#N)CCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2;m1_m2_m3_m4:[N-]=[N+]=[N-].[Na+];m1_m2_m3_m4:[Cl-].[NH4+];m1_m2_m3_m4:CN(C=O)C, Reagents are:m5:O, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCC2=NN=NN2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (1.20 g), sodium azide (1.09 g), ammonium chloride (0.90 g) and N,N-dimethylformamide (30 ml) was stirred at 130° to 140° C. for 16 hours. The reaction mixture was poured over water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with methanol-chloroform (5:95, v/v), 5-[2-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]ethyl ]-1H-tetrazole (1.05 g, 78%) was obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 177° to 178° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=C2C(NC(S2)=O)=O)C=C1, Reagents are:m1_m2_m3:[C].[Pd];m1_m2_m3:O1CCCC1, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-[6-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione (0.80 g), palladium-carbon (5%, 1.60 g) and tetrahydrofuran (250 ml) was subjected to catalytic reduction at room temperature under a hydrogen pressure of 3.2 kgf/cm2 for 8 hours. After the catalyst was filtered off, the filtrate was subjected to catalytic reduction under constant conditions for additional 16 hours. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:5, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-thiazolidinedione (0.305 g, 38%) were obtained, which was then recrystallized from dichloromethane-methanol to yield yellow needles having a melting point of 179° to 180° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1;m1_m2_m3_m4:O1C(NC(C1)=O)=O;m1_m2_m3_m4:N1CCCC1;m1_m2_m3_m4:C(C)O, Reagents are:m5:O, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(O2)=O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde (1.70 g), 2,4-oxazolidinedione (1.55 g), pyrrolidine (0.365 g) and ethanol (40 ml) was heated under refluxing conditions for 3 hours. The reaction mixture was poured over water; the resulting crystals were collected by filtration. The crystals were dissolved in tetrahydrofuran (100 ml); after palladium-carbon (0.40 g) was added, the mixture was subjected to catalytic reduction at room temperature under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated under reduced pressure; the residue was subjected to silica gel column chromatography. From the fraction eluted with methanolchloroform (2:98, v/v), crystals of 5-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranylmethyl]-2,4-oxazolidinedione (0.14 g, 6.6%) were obtained, which was then recrystallized from dichloromethane-methanol to yield colorless prisms having a melting point of 172° to 173° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)CCCO)C1;m2:[C-]#N.[Na+], Reagents are:, and Products are 0:C(#N)CCCC=1OC2=C(C1)C=C(C=C2)OCC=2N=C(OC2C)C2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In the same manner as in Example 13, 3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol was mesylated and then reacted with sodium cyanide to yield 2-(3-cyanopropyl)-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (yield 80%), which was then recrystallized from acetone-isopropyl ether to yield colorless prisms having a melting point of 114° to 115° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(=O)C1=C(OCC(=O)OC)C=C(C=C1)OC;m1_m2_m3:C1CCC2=NCCCN2CC1, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:COC1=CC2=C(C=C(O2)C(=O)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of methyl 2-formyl-5-methoxyphenoxyacetate (27.7 g), 1,8-diazabicyclo[5.4.0]-7-undecene (40.8 g) and toluene (200 ml) was heated under refluxing conditions for 4 hours. The reaction mixture was concentrated under reduced pressure; after 6N hydrochloric acid was added, the residue was extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; 10% hydrochloric acid-methanol (30 ml) was added to the residue, followed by heating at 70° to 80° C. for 4 hours. The reaction mixture was concentrated under reduced pressure; water was added, followed by extraction with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with chloroform-hexane (1:2, v/v), methyl 6-methoxybenzofuran-2-carboxylate (14.3 g, 57%) was obtained, which was then recrystallized from dichloromethane-isopropyl ether to yield colorless prisms having a melting point of 97° to 98° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CO)C=C1, Reagents are:m1_m2_m3:[O-2].[O-2].[Mn+4];m1_m2_m3:O1CCCC1, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-methanol (21.0 g), activated manganese dioxide (52.0 g) and tetrahydrofuran (800 ml) was stirred at 60° to 65° C. for 6 hours. After the insoluble portion was filtered off, the filtrate was concentrated; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (2:98, v/v), crystals of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-carbaldehyde (14.3 g, 69%) were obtained, which was then recrystallized from dichloromethane-isopropyl propyl ether to yield colorless prisms having a melting point of 137° to 138° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C(=O)OCC)C=C1, Reagents are:m1_m2_m3:O1CCCC1;m1_m2_m3:[C].[Pd], and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCCO)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (E)-ethyl 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate (1.30 g) in tetrahydrofuran (50 ml), palladium-carbon (5%, 0.70 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, sodium borohydride (0.61 g) was added to the filtrate, followed by dropwise addition of methanol (10 ml) under refluxing conditions. After heating under refluxing conditions for 1 hour, the reaction mixture was poured over water and neutralized with 2N hydrochloric acid, followed by extraction with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:5, v/v), 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol was obtained as an oily substance (0.90 g, 77%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C/C=C/O)C=C1, Reagents are:m1_m2_m3:[O-2].[O-2].[Mn+4];m1_m2_m3:ClCCl, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of (E)-3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propen-1-ol (3.85 g), activated manganese dioxide (8.00 g) and dichloromethane (150 ml ) was stirred at room temperature for 2 hours. After the insoluble portion was filtered off, the filtrate was concentrated to yield crystals of (E)-3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrolein (3.40 g, 89%), which was then recrystallized from dichloromethane-isopropyl ether to yield colorless prisms having a melting point of 132° to 133° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:COC1=CC=C(C(C=O)=C1)O;m1_m2:BrCC(=O)OC, Reagents are:, and Products are 0:C(=O)C1=C(OCC(=O)OC)C=CC(=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In the same manner as in Reference Example 1, 5-methoxysalicylaldehyde was reacted with methyl bromoacetate to yield methyl 2-formyl-4-methoxyphenoxyacetate (yield 86%), which was then recrystallized from acetone-hexane to yield colorless prisms having a melting point of 74° to 75° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:OC=1C=CC2=C(C=C(O2)C(=O)OC)C1;m1_m2:ClCC=1N=C(OC1C)C1=CC=CC=C1, Reagents are:, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)C(=O)OC)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In the same manner as in Reference Example 4, methyl 5-hydroxybenzofuran-2-carboxylate was reacted with 4-chloromethyl-5-methyl-2-phenyloxazole to yield methyl 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)bezofuran-2-carboxylate (yield 87%), which was then recrystallized from acetone-ethyl acetate to yield colorless prisms having a melting point of 177° to 178° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/C(=O)OCC)C1;m2:[H-].C(C(C)C)[Al+]CC(C)C, Reagents are:, and Products are 0:CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/CO)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In the same manner as in Reference Example 11, (E)-ethyl 3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate was reduced with diisobutylaluminum hydride to yield (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (yield 90%), which was then recrystallized from ethyl acetate-hexane to yield colorless prisms having a melting point of 145° to 146° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/CO)C1, Reagents are:m1_m2_m3:O1CCCC1;m1_m2_m3:[C].[Pd], and Products are 0:CC=1C=CC=C(C1)C(OC=1C=CC2=C(C=C(O2)CCCO)C1)C=1N=COC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (2.00 g) in tetrahydrofuran (100 ml), palladium-carbon (5%, 0.30 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated to yield 3-[5-(5-methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol (yield 93%), which was then recrystallized from acetone-isopropyl ether to yield colorless prisms having a melting point of 101° to 102° C. |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)O;m3:S(=O)([O-])[O-].[Na+].[Na+];m1_m6_m2:[O-][Mn](=O)(=O)=O.[K+];m1_m6_m2:CC(=O)C1=CC=C(C=C1)SC, Reagents are:m5:O;m1_m6_m2:O, and Products are 0:CC(=O)C1=CC=C(C=C1)S(=O)(=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 152 g (0.96 mol) of KMnO4 in 3.5 1 of water is introduced into a mixture of 117.1 g (0.7 mol) of 4-(methylthio)acetophenone, prepared in Example 2c, and 292 ml of acetic acid. 2.3 l of water are added and the reaction temperature is allowed to return to room temperature. Saturated sodium sulfite solution is added dropwise until the solution is decolorized. This is left to stand overnight at room temperature. The solid obtained is filtered off, washed copiously with water and recrystallized from 95% ethanol to give 91.5 g of 4-(methylsulfonyl)acetophenone. |
Here is a chemical reaction formula: Reactants are:m2:N1N=CC=C1;m3_m4:C(C)N(CC)CC;m3_m4:C1(CCCCC1)C(=O)Cl;m1:COC1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)(=O)=O;m5:C([O-])([O-])=O.[Na+].[Na+], Reagents are:m6:C(Cl)Cl, and Products are 0:COC1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OC(=O)C1CCCCC1)CC)(=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: As a starting material, 4-methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide corresponding to pyrazole derivative (I-H) was used. 0.4 Gram (1.1 mmol) thereof was dissolved in 4 ml of methylene chloride, and 0.22 g (2.2 mmol) of triethylamine as a base and 0.19 g (1.3 mmol) of cyclohexylcarbonyl chloride corresponding to compound B-A-Hal as a reaction reagent were added. The mixture was allowed to react at room temperature for 8 hours. A saturated sodium carbonate aqueous solution was added to the reaction mixture, and the resultant mixture was extracted with ethyl acetate. An organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant oil was purified by flush column chromatography (Wako Gel C-300; hexane/ethyl acetate=1:1) to give 0.28 g (yield 54%) of 4-methoxy-5-methyl-6-(5-cyclohexylcarbonyloxy-1-ethylpyrazol-4-yl)carbonylthiochroman-1,1-dioxide. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:CON=C1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)(=O)=O;m1_m2_m3_m4_m5:N1N=CC=C1;m1_m2_m3_m4_m5:C(C(=O)C1=CC=CC=C1)Br;m1_m2_m3_m4_m5:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m4_m5:CC(=O)C, and Products are 0:CON=C1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OCC(=O)C1=CC=CC=C1)CC)(=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.4 Gram (1.1 mmol) of 4-methoxyimino-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide corresponding to pyrazole derivative (I-H), 0.23 g (1.2 mmol) of phenacyl bromide corresponding to compound B-A-Hal and 0.15 g of potassium carbonate were added to 10 ml of acetone, and the mixture was stirred under heat for 8 hours. Insolubles were removed by filtration, and then the acetone was distilled off. The residue was dissolved in ethyl acetate, and the mixture was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The ethyl acetate was distilled off under reduced pressure, and the residue was subjected to column chromatography (hexane/ethyl acetate) to give 4-methoxyimino-5-methyl-6-(1-ethyl-5-phenacyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ib-2) at a yield of 52%. |
Here is a chemical reaction formula: Reactants are:m4:OC1=CC=NN1;m1:CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)O)C)(=O)=O)C;m6:C([O-])([O-])=O.[K+].[K+];m5:C1(CCCCC1)N=C=NC1CCCCC1;m2:S1C(CCC2=CC=CC=C12)C(=O)O;m3:C(C)N1N=CC=C1O, Reagents are:m7:C(C)(C)(CC)O, and Products are 0:CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.4 Grams (0.026 mol) of 4,4,5,8-tetramethylthiochroman-6-carboxylic acid-1,1-dioxide corresponding to thiochroman carboxylic acid (IIIc), 3.4 g (0.03 mol) of 1-ethyl-5-hydroxypyrazole corresponding to 5-hydroxypyrazole (II) and 6.22 g (0.03 mol) of DCC (N,N'-dicyclohexylcarbodiimide) were all together added to 50 ml of tert-amyl alcohol, and the mixture was stirred at room temperature for 30 minutes. Then, 1.8 g (0.013 mol) of anhydrous potassium carbonate was added. The reaction mixture was allowed to react at 80° C. for 8 hours, and the reaction solvent was distilled off under reduced pressure. The resultant residue was dispersed in a 5% potassium carbonate aqueous solution and ethyl acetate to separate it into two layers. Further, the aqueous layer was adjusted to a pH of 1 with 5% hydrochloric acid, and the formed solid was recovered by filtration to give 6.13 g (yield 62%) of 4,4,5,8-tetramethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-1). |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C;m1_m2:N1N=CC=C1;m4_m7:C(C)S(=O)(=O)Cl;m3_m6:C([O-])([O-])=O.[K+].[K+], Reagents are:m5:C(Cl)Cl;m4_m7:[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC;m3_m6:O, and Products are 0:CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1OS(=O)(=O)CC)CC)C)(=O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.7 Gram (1.9 mmol) of the 4,4,5,8-tetramethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-1) corresponding to pyrazole derivative (I-H), obtained in Referential Production Example 5, was dissolved in 8 ml of methylene chloride. Then, a solution of 0.51 g (3.8 mmol) of potassium carbonate in 5 ml of water was added, and further, 0.49 g (3.8 mmol) of ethanesulfonyl chloride and 0.05 g (0.2 mmol) of benzyltriethylammonium chloride, corresponding to compound B-A-Hal, were added. The mixture was allowed to react at room temperature for 2 hours, and further refluxed under heat for 2 hours. The reaction mixture was allowed to cool, and then a methylene chloride layer was recovered and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant oil was purified by silica gel column chromatography to give 0.73 g (yield 82%) of 4,4,5,8-tetramethyl-6-(1-ethyl-5-ethanesulfonyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-2). |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)O;m4:[Cl-].[Na+];m1_m5_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m5_m2:C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=C(C=CC=C1)OC)C(=O)OC, Reagents are:m6:O1CCCC1;m1_m5_m2:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=C(C=CC=C1)OC)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 560 mmol of lithium aluminum hydride in 800 ml of tetrahydrofuran (THF), under a nitrogen atmosphere and at 5° C., are added 225 mmol of methyl [trans-1-benzyl-4-(2-methoxyphenyl)pyrrolidin-3-yl]carboxylate (described in Preparation A) dissolved in 500 ml of THF. After stirring for 1 hour at 5° C., 139 ml of isopropyl alcohol are added slowly to the above mixture, followed by 85.2 ml of saturated sodium chloride solution. The mixture is stirred slowly at room temperature. After filtration and evaporation of the solvents, the expected product is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m3_m2:C(C1=CC=CC=C1)N1C[C@H]2[C@@H](C1)C1=C(OC2=O)C=C(C=C1)OC, Reagents are:m1_m3_m2:C1CCOC1, and Products are 0:C(C1=CC=CC=C1)N1C[C@H]([C@H](C1)C1=C(C=C(C=C1)OC)O)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 230 mmol of lithium aluminum hydride in 800 ml of THF, under a nitrogen atmosphere, are added 180 mmol of cis-2-benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one, described in Preparation G, at +5° C. The reaction medium is maintained at +10° C. for one hour before being hydrolyzed, and is filtered on Celite. The organic phase is dried and, after evaporation, gives the expected product. |
Here is a chemical reaction formula: Reactants are:m4_m5:Cl;m1_m2_m3:C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)C(C#N)C(C)=O;m1_m2_m3:C(C)O;m1_m2_m3:C(C)OC(CNN)OCC, Reagents are:m6:C(C)(=O)OCC;m4_m5:O1CCOCC1, and Products are 0:Cl.NC1=CC=C(C=C1)C1=C2N(N=C1C)C=CN2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2.5 g of 2-(4-t-butoxycarbonylaminophenyl)-3-oxobutyronitrile, 20 ml of ethanol and 1.4 g of 2,2-diethoxyethylhydrazine was heated under reflux for 2 hours. 20 ml of 4N hydrogen chloride in dioxane were added, and then the whole mixture was heated under reflux for a further 30 minutes. After the mixture had been cooled, ethyl acetate was added to precipitate crystals. These crystals were collected by filtration and recrystallized from ethanol to give 1.4 g of the title compound as pale brown plates melting at 180°-190° C. |
Here is a chemical reaction formula: Reactants are:m1:S(=O)(=O)(Cl)Cl;m2:C1(=CC=CC=C1)OCC1=CC=CC=C1, Reagents are:m3:CN(C)C=O, and Products are 0:C(C1=CC=CC=C1)OC1=CC=C(C=C1)S(=O)(=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 1.12 portion of anhydrous DMF is cooled to 0° C. and treated dropwise with 2.06 g of sulfuryl chloride. The resulting suspension is stirred for 30 min., then treated with 1.50 g of benzyl phenyl ether. The mixture is heated at 90° C. for 3 h, then cooled, extracted with brine and methylene chloride, and dried over MgSO4. Chormotography on silica gel (i-PrOH/hexanes) yields 4-benzyloxybenzenesulfonyl chloride. |
Here is a chemical reaction formula: Reactants are:m4:N;m3:CN(C)C=O;m2:S(=O)(Cl)Cl;m1:C1(CCCC1)CC(=O)O, Reagents are:m5:ClCCl, and Products are 0:C1(CCCC1)CC(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cyclopentylacetic acid (5.2 g, 41 mmol) and thionyl chloride (10 mL) were combined then DMF (0.2 mL) was added and the solution was stirred 1.5 h at R.T. Dichloromethane (10 mL) was added and the solution cooled in an ice bath whereupon 25% aqueous ammonia (30 mL) was added and the mixture stirred for 0.5 h. The solution was extracted with CH2Cl2 (3×) and the combined extracts washed with 1N HCl, dried over MgSO4, and concentrated to give cyclopentylacetamide (2.699 g, 52%). [1H]-NMR(CDCl3) consistent with structure. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:N1CCC(CC1)C(=O)N;m1_m3_m2:C(C1=CC=CC=C1)Br, Reagents are:m1_m3_m2:CS(=O)C;m4:CCOC(=O)C, and Products are 0:C(C1=CC=CC=C1)NC(=O)C1CCNCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Piperidinecarboxamide (10.2 g, 78.0 mmol) in DMSO (10 mL) was treated with benzyl bromide (20.0 mL, 168 mmol). The mixture was diluted with EtOAc and washed with 1N aq. HCl, 5N aq. NaOH, dried over MgSO4, and concentrated to give 5.90 g (35%) of N-benzyl-4-piperidinecarboxamide. [1H]-NMR(CDCl3) consistent with structure. |
Here is a chemical reaction formula: Reactants are:m0_m4:C(Cl)(Cl)Cl.CO;m1_m2_m5_m3:OC1CCNCC1;m1_m2_m5_m3:CCN(CC)CC;m1_m2_m5_m3:ClC(=O)OCC1=CC=CC=C1, Reagents are:m1_m2_m5_m3:C(Cl)Cl, and Products are 0:C(=O)(OCC1=CC=CC=C1)N1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Hydroxypiperidine (10.8 g, 107 mmol) and Et3N (17 mL, 123 mmol) in 80 mL of CH2Cl2 was cooled in an ice bath whereupon benzyl chloroformate (16.3 mL, 114 mmol) was added. After stirring 1.5 h at R.T. the mixture was subjected to standard work-up conditions to give 13.9 g (55%) of N-Cbz-piperidine after chromatography (CHCl3 /MeOH; 10:1). [1H]-NMR(CDCl3) consistent with structure. |
Here is a chemical reaction formula: Reactants are:m3:C(=O)(OCC1=CC=CC=C1)N1CCCCC1;m4:C1(C=2C(C(N1)=O)=CC=CC2)=O;m1_m5_m2:CCOC(=O)/N=N/C(=O)OCC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m1_m5_m2:C1CCOC1;m6:C1CCOC1, and Products are 0:C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)N1C(C=2C(C1=O)=CC=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of DEAD (1.61 mL, 10.2 mmol) in 20 mL of THF was added to a solution of triphenylphosphine (2.69 g, 10.3 mmol), the N-Cbz-piperidine prepared in Example 16A (2.36 g, 100 mmol) and phthalimide (1.50 g, 10.2 mmol) in 80 mL of THF. After stirring 10.5 h at R.T. the mixture was quenched with water, extracted with EtOAc (3×) and the combined extracts washed with brine solution, dried over Na2SO4 and concentrated to give the crude product. Purification of this material by chromatography (hexanes/EtOAc; 2:1) gave 1.81 g, (50%) of 1-benzyloxycarbonyl-4-phthalimidylpiperidine. [1H]-NMR(CDCl3) consistent with structure. |
Here is a chemical reaction formula: Reactants are:m5_m3:C(=O)([O-])[O-].[K+].[K+];m2:O.NN;m1:C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)N1C(C=2C(C1=O)=CC=CC2)=O, Reagents are:m5_m3:[Cl-].[Na+].O;m4:C(C)O, and Products are 0:NC1CCN(CC1)C(=O)OCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Benzyloxycarbonyl-4-phthalimidylpiperidine (1.50 g, 4.27 mmol), prepared in Example 16B, was taken up in 20 mL of ethanol. To this solution was added hydrazine monohydrate (35 mL, 700 mmol) and this mixture was heated at 100° C. for 3 h. Brine solution (40 mL) and 10% aq. K2CO3 (60 mL) were added and the mixture was extracted with 5% MeOH/CHCl3 (3×). The combined extracts were washed with 2N aq. HCl, 2N aq. NaOH, brine solution, dried over Na2SO4 and concentrated to give 0.847 g, (85%) of 4-amino-1-benzyloxycarbonylpiperidine. [1H]-NMR(CDCl3) consistent with structure. |
Here is a chemical reaction formula: Reactants are:m1_m2_m6_m3:CC(=O)C1=C(C=CC=C1OC)OC;m1_m2_m6_m3:C(C(=O)[O-])(=O)OCC;m1_m2_m6_m3:C[O-].[Na+];m5:C(C)(C)OC(C)C;m4_m7:[Na], Reagents are:m1_m2_m6_m3:CO;m4_m7:CO, and Products are 0:[Na+].COC1=C(C(=CC=C1)OC)C(=CC(C(=O)OC)=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 100 g of 2,6-dimethoxyacetophenone and 7.5 ml of ethyl oxalate in 520 ml of anhydrous MeOH is added slowly to a solution of sodium methylate prepared from 12.7 g of sodium and 285 ml of anhydrous MeOH. The reaction mixture is heated to reflux for 7 hours and left overnight at RT. It is poured into 2 litres of isopropyl ether and left stirring for 15 minutes. The expected product is obtained by filtration, washing with isopropyl ether and drying under vacuum, m=120 g, m.p.=178° C. |
Here is a chemical reaction formula: Reactants are:m3_m6:Cl[Sn]Cl;m1_m4:N(=O)[O-].[Na+];m2_m5:NC1=CC=C(C=2CCCCC12)C(=O)O, Reagents are:m3_m6:Cl;m1_m4:O;m2_m5:Cl, and Products are 0:Cl.N(N)C1=CC=C(C=2CCCCC12)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 0.26 g of NaNO2 in 1 ml of water is added to a solution, cooled to -5° C., of 0.73 g of 4-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid in 10 ml of concentrated HCl. After one and a half hours of stirring at -5° C., a solution of 3.4 g of SnCl2 ·2H2O in 34 ml of concentrated HCl is added at -5° C. The mixture is stirred for 1 hour at RT and filtered, and the product is washed with concentrated HCl and dried under a stream of dry nitrogen to obtain 0.67 g of the expected hydrazine. |
Here is a chemical reaction formula: Reactants are:m2_m5:NC1=C(C(=C(C(=O)O)C=C1)C)C;m3_m6:Cl[Sn]Cl;m1_m4:N(=O)[O-].[Na+], Reagents are:m2_m5:Cl;m3_m6:Cl;m1_m4:O, and Products are 0:Cl.CC1=C(C(=O)O)C=CC(=C1C)NN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.87 g of NaNO2 in 7 ml of water is added slowly to a solution, cooled to -5° C., of 4.5 g of 4-amino-2,3-dimethylbenzoic acid in 135 ml of concentrated HCl. After 2 hours of stirring at -5° C., a solution of 25 g of SnCl2 ·2H2O in 250 ml of concentrated HCl is added at -10° C., and the mixture is stirred for 30 minutes at -5° C. and then 2 hours at RT. The mixture is filtered, and the precipitate is washed with 5 ml of concentrated HCl and dried under a stream of dry nitrogen and then under vacuum to obtain 5.5 g of expected product. |
Here is a chemical reaction formula: Reactants are:m3_m6_m7:Cl[Sn]Cl;m2_m5:NC=1C=CC(=C(C(=O)O)C1)Cl;m1_m4:N(=O)[O-].[Na+], Reagents are:m3_m6_m7:Cl;m3_m6_m7:O;m2_m5:Cl;m1_m4:O, and Products are 0:Cl.N(N)C=1C=CC(=C(C(=O)O)C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2.11 g of NaNO2 in 40 ml of water is added over 30 minutes to a suspension, cooled to -2° C., of 5 g of 5-amino-2-chlorobenzoic acid in 50 ml of concentrated HCl. The solution is stirred for 2 hours at -3° C. and cooled to -10° C., and a solution of 23 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ml of water is added over 30 minutes. The mixture is stirred for one and a half hours at 0° C. and filtered, and the precipitate is dried to obtain 4 g of expected product. |
Here is a chemical reaction formula: Reactants are:m3:O.NN;m1_m2_m4:FC1=C(C=C(C=C1)[N+](=O)[O-])C;m1_m2_m4:O.NN, Reagents are:m1_m2_m4:CC(C)O, and Products are 0:F.N(N)C1=C(C=C(C=C1)[N+](=O)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.6 g of 1-fluoro-2-methyl-4-nitrobenzene and 3 ml of hydrazine hydrate in 45 ml of 2-propanol is heated to reflux for 2 hours. 3 ml of hydrazine hydrate are added, refluxing is continued for 2 hours and the mixture is left overnight with stirring at RT. The precipitate formed is drained. 3.53 g of the expected product are obtained, m.p.=182° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC=C;m4_m3:[OH-].[NH4+], Reagents are:m4_m3:CO, and Products are 0:C(=C)O;0:C(C)(=O)OC=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: This Example shows the preparation of high TFE content copolymer. The conditions of Example III were repeated except that a total of 470 mg of APS was added, the TFE addition rate was 0.01 lb/min (4.5 g/min), the vinyl acetate addition rate was 2 ml/min., and the final agitation rate was 80 rpm. 2580 g of a 25.0 wt % solids colloidal dispersion was obtained. To 100 g of the isolated, dried polymer was added 500 ml of methanol and 40 ml of concentrated ammonium hydroxide. After several weeks at room temperature with occasional shaking, the resulting solution was heated to remove the reaction by-products and there was obtained a hazy, viscous solution of 19 wt % solids of approximate composition 82 wt % TFE, 16 wt % vinyl alcohol, and 2 wt % vinyl acetate. Upon evaporation of the solvent at 50° C. in a vacuum oven for one day, a clear, somewhat rubbery melt fabricable polymer was obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(O)CN;m1_m2:C(C)O;m3_m4:C(C)O;m3_m4:O1C(COCCCCCCCCCCCC(=O)OCCCC)C1, Reagents are:m5:O, and Products are 0:OC(COCCCCCCCCCCCC(=O)OCCCC)CNCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml flask equipped with a stirrer and dropping funnel was charged with 23.7 g (250 mmol) of ethanolamine and 23.7 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 8.20 g (25 mmol) of butyl 12-(2,3-epoxypropoxy)-dodecanate was added dropwise over 1 hour. After completion of the reaction, water was added to the reaction mixture, followed by extraction with chloroform. The resultant chloroform solution was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 5.40 g (yield: 55.4%) of the title compound (Ia-15). |
Here is a chemical reaction formula: Reactants are:m1_m4:C(O)CN;m3_m2:O1CC1(COCCCCCCCCCCCCCC)C, Reagents are:m1_m4:C(C)O;m3_m2:C(C)O, and Products are 0:OCCNCC(COCCCCCCCCCCCCCC)(O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml flask equipped with a stirrer and dropping funnel was then charged with 16.8 g (280 mmol) of ethanolamine and 15 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 5.00 g (17.6 mmol) of 1,2-epoxy-2-methyl-3-tetradecyloxypropane was added dropwise over 3 hours. The contents were stirred further for 2 hours. The resultant reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 4.13 g (yield: 68%) of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(O)CN;m1_m2:C(C)O;m3:O1CC1CCCCCCCCCCCCCCCC, Reagents are:m4:O, and Products are 0:OCCNCC(CCCCCCCCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 300-ml flask equipped with a stirrer and a dropping funnel was charged with 45.8 g (0.75 mol) of ethanolamine and 9 g of ethanol. While stirring the mixture at 80° C., 13.4 g (50 mmol) of 1,2-epoxyoctadecane were added dropwise over 2 hours. Water was added to the resultant reaction mixture, and white crystals formed were collected by filtration, washed with water and then recrystallized from methanol, thereby obtaining 12.3 g (yield: 74.6%) of the title compound (IIc-1). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:O1CC1CCCCCCCCCCCCCCCC;m1_m2_m3:CNCCO, Reagents are:m1_m2_m3:C(C)O, and Products are 0:OCCN(C)CC(CCCCCCCCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 300-ml flask equipped with a stirrer was charged with 26.85 g (0.1 mol) of 1,2-epoxyoctadecane, 7.51 g (0.1 mol) of N-methylethanolamine and 50 ml of ethanol, and the contents were stirred at 80° C. for 18 hours. After the solvent was distilled off under reduced pressure, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 23.0 g (yield: 67%) of the title compound (IIc-2). |
Here is a chemical reaction formula: Reactants are:m1_m4:C(O)CN;m3_m2:C(CCCCCCCCCCCCC)OCC1C(C)(C)O1, Reagents are:m1_m4:C(C)O;m3_m2:C(C)O, and Products are 0:OCCNC(C(C)(O)C)COCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml two-necked flask equipped with a stirrer and a dropping funnel was charged with 15.3 g (16.7 mmol) of ethanolamine and 5.0 g of ethanol. While heating and stirring the mixture at 80° C. in a nitrogen atmosphere, an ethanol solution of 5.00 g (16.7 mmol) of 1-tetradecyloxy-3-methyl-2-butene oxide was added dropwise over 3 hours. After heating and stirring the mixture further for 16 hours, the resultant reaction mixture was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 3.47 g (yield: 58%) of the title compound (IIc-4). |
Here is a chemical reaction formula: Reactants are:m1_m6:[H-].[H-].[H-].[H-].[Li+].[Al+3];m2:N#N;m4:[OH-].[K+];m5_m3:C(CCCCCCCC=CCCCCCCCC)(=O)NCCO, Reagents are:m1_m6:O1CCCC1;m5_m3:O1CCCC1, and Products are 0:C(CCCCCCCC=CCCCCCCCC)NCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml eggplant type flask equipped with a stirrer was charged with 1.40 g (37.2 mmol) of LiAlH4 and 30 ml of tetrahydrofuran. While heating and stirring the contents at room temperature in an N2 atmosphere, a tetrahydrofuran solution of 1.67 g (5.12 mmol) of N-(9-octadecenoyl)ethanolamine was added dropwise over 10 minutes. After the mixture was heated to 60° C. and stirred for 16 hours, the resultant reaction mixture was cooled to room temperature, and 14 g of 5% aqueous KOH. After a salt deposited was separated by filtration, the filtrate was concentrated under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 0.96 g (yield: 65%) of the title compound (IIc-6). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N(CCO)CCO;m1_m2_m3:C1CCCCCCCC(=O)OCCCCCCC1, Reagents are:m4:O;m1_m2_m3:C[O-].[Na+], and Products are 0:OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 200-ml flask equipped with a stirrer was charged with 16.6 g (158 mmol) of diethanolamine and 20.1 g (79 mmol) of cyclohexadecanolide, to which 0.21 g (3.9 mmol) of sodium methoxide was added. The contents were stirred at 80° C. for 18 hours. After completion of the reaction, water was added, and solids deposited were collected by filtration and recrystallized from methanol, thereby obtaining 23.3 g (yield: 82%) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide. |
Here is a chemical reaction formula: Reactants are:m2_m3:N#N;m2_m3:OCCN(C(CCCCCCCCCCCCCCCO)=O)CCO;m1_m5:[H-].[H-].[H-].[H-].[Li+].[Al+3];m4:[OH-].[K+], Reagents are:m1_m5:O1CCCC1, and Products are 0:OCCN(CCO)CCCCCCCCCCCCCCCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml flask equipped with a stirrer and reflux condenser was charged with 3.01 g (79.3 mmol) of LiAlH4 and 200 ml of tetrahydrofuran. While stirring the mixture at room temperature in an N2 atmosphere, 5.00 g (13.9 mmol) of N,N-bis(2-hydroxyethyl)-16-hydroxyhexadecanamide were added, followed by stirring at 65° C. for 18 hours. After cooling the reaction mixture to room temperature, 15 g of 3% aqueous KOH were added, and a salt deposited was separated by filtration. The solvent was then distilled off under reduced pressure, and the resultant residue was purified by column chromatography on silica gel, thereby obtaining 2.98 g (yield: 62%) of the title compound (IId-3). |
Here is a chemical reaction formula: Reactants are:m3:N(CCO)CCO;m1_m2:C(O)CN;m1_m2:O1C(CCCC1)OCCCCCCCCCCCCCCCC(=O)OC;m4:C1CCCCCCCC(=O)OCCCCCCC1, Reagents are:, and Products are 0:OCCNCCCCCCCCCCCCCCCCOC1OCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A reaction was conducted in the same manner as in Preparation Example 37 except that ethanolamine and methyl 16-(2-tetrahydropyranyloxy)hexadecanate were used in place of diethanolamine and cyclohexadecanolide, respectively, in Preparation Example 37, thereby obtaining the title compound (IId-4). |
Here is a chemical reaction formula: Reactants are:m1_m4:C(O)CN;m2_m3:C(CCCCCCCCCCCCC)SCC1CO1, Reagents are:m1_m4:C(C)O;m2_m3:C(C)O, and Products are 0:OCCNCC(CSCCCCCCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 300-ml flask equipped with a stirrer and dropping funnel was charged with 61.1 g (1 mol) of ethanolamine and 61 g of ethanol. While stirring the contents at 80° C., a solution of 14.3 g (50 mmol) of 1-tetradecylthio-2,3-epoxypropane in 30 g ethanol was added dropwise over 3 hours. After completion of the dropping, the resultant reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from hexane, thereby obtaining 15.8 g (yield: 91%) of the title compound (IIe-1). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:CNCCO;m1_m3_m2:C(CCCCCCCCCCCCC)(=O)OCC1CO1, Reagents are:m1_m3_m2:C(C)O, and Products are 0:C(CCCCCCCCCCCCC)(=O)OCC(CN(C)CCO)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml flask equipped with a stirrer and dropping funnel was charged with 6.01 g (80 mmol) of N-methylethanolamine, 50 ml of ethanol and 22.8 g (80 mmol) of glycidyl tetradecanate, and the contents were stirred at 80° C. for 2 hours. The resultant reaction mixture was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel, thereby obtaining 17.5 g (yield: 60.8%) of the title compound (IIe-2). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C=CC(CCCCCCCCCC)O;m1_m2_m3:ClC1=CC(=CC=C1)C(=O)OO;m1_m2_m3:C1=CC=CC=C1, Reagents are:m4:CCCCCC, and Products are 0:O1CC1C(CCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml flask equipped with a stirrer was charged with 23.8 g (0.12 mol) of 1-tridecen-3-ol, 25.0 g (0.145 mol) of m-chloroperbenzoic acid and 250 ml of benzene, and the contents were stirred at room temperature for 48 hours. After completion of the reaction, 200 ml of hexane. Solids deposited were separated by filtration, and the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography on silica gel, thereby obtaining 19.0 g (yield: 74%) of 1,2-epoxy-3-tridecanol. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)N;m1_m2_m3:O1CC1C(CCCCCCCCCC)O, Reagents are:m1_m2_m3:O1CCOCC1, and Products are 0:C(C1=CC=CC=C1)NCC(C(CCCCCCCCCC)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml flask equipped with a stirrer was charged with 107 g (1 mol) of benzylamine, to which a solution of 5.2 g (71 mmol) of 1,2-epoxy-3-tridecanol in 170 ml of dioxane was added dropwise over 2 hours. After completion of the dropping, a reaction was conducted further for 12 hours at 80° C. Dioxane and excess benzylamine were distilled off under reduced pressure. The resultant residue was recrystallized from hexane, thereby obtaining 16.4 g (yield: 72%) of the title compound (IIh-1). |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CC=CC=C1)N;m1_m2:O1CC1CCCCCCCCCCCCCCCC, Reagents are:, and Products are 0:NCC(CCCCCCCCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500-ml flask equipped with a stirrer was charged with 160 g (1.5 mol) of benzylamine, to which 29 g (0.11 mol) of 1,2-epoxyoctadecane were added dropwise over 3 hours while stirring at 100° C. Stirring was conducted further for 12 hours at 100° C. Benzyl alcohol was distilled off under reduced pressure, and the residue was charged into a 500-ml autoclave, to which 300 ml of ethanol and 10 g of 5% Pd/C were added to conduct hydrogenolysis for 48 hours at room temperature under a hydrogen pressure of 5 atm. After the catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from hexane, thereby obtaining 26.1 g (yield: 83%) of the title compound (IIh-7). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:C(C(CCCCCCCCCCCCCCCC)O)O;m1_m2_m5:C1(=CC=C(C=C1)S(=O)(=O)O)C;m3:O1CCCC=C1;m4:C(=O)(O)[O-].[Na+], Reagents are:m1_m2_m5:ClCCl, and Products are 0:O1C(CCCC1)OCC(CCCCCCCCCCCCCCCC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 1-liter flask equipped with a stirrer and dropping funnel was charged with 20 g (70 mmol) of octadecane-1,2-diol, 0.7 g (3.5 mmol) of p-toluenesulfonic acid and 350 ml of dichloromethane. While stirring the contents at room temperature, 5.9 g (70 mmol) of dihydropyran were added dropwise. After stirring the mixture at room temperature for 30 minutes, it was neutralized with NaHCO3 and concentrated under reduced pressure, and the resultant residue was then purified by column chromatography on silica gel, thereby obtaining 7.5 g (yield[: 29%) of 1-(2-tetrahydropyranyloxy)-2-octadecanol. This compound was charged into a 200-ml flask equipped with a stirrer, to which 5.1 g (50 mmol) of triethylamine and 50 ml of dichloromethane were added. Further, 3.8 g (33 mmol) of methanesulfonyl chloride were added at room temperature with stirring. After the resultant mixture was stirred at room temperature for 14 hours, the reaction mixture was added with water and subjected to extraction with dichloromethane, and the solvent was distilled off under reduced pressure. The resultant residue and 15 ml of dimethylformamide was charged into a 100-ml flask equipped with a stirrer, to which 5.5 g (83 mmol) of NaN3 were added. The contents were stirred at 90° C. for 1.5 hours. After cooling the reaction mixture to room temperature, it was added with water and subjected to extraction with chloroform, followed by concentration under reduced pressure. Thereafter, the resultant residue was purified by column chromatography on silica gel, thereby obtaining 7.1 g (yield: 90%) of an azide intermediate. |
Here is a chemical reaction formula: Reactants are:m1_m4:NCC(CN)O;m2:N#N;m5_m3:OCCCCCCCCCCCC(=O)OC, Reagents are:m1_m4:C[O-].[Na+];m5_m3:C1CCOC1, and Products are 0:NCC(CNC(CCCCCCCCCCCO)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 100-ml two-necked flask equipped with a stirrer and dropping funnel was charged with 9.39 g (104 mmol) of 1,3-diamino-2-propanol and 0.047 g (0.87 mmol) of sodium methoxide. While heating and stirring the contents at 80° C. in an N2 atmosphere, a THF solution of 4.00 g (17.4 mmol) of methyl 12-hydroxydodecanate was added dropwise over 2.5 hours. Precipitate formed was washed with water and recrystallized from ethyl acetate-methanol (4:1 v/v), thereby obtaining 3.80 g (yield: 75%) of the title compound (IIh-12) as colorless powder. |
Here is a chemical reaction formula: Reactants are:m1:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O;m2:C(C1=CC=CC=C1)Br, Reagents are:, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 11, by reacting 12.5 g (35 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene with 5 ml (42 mmol) of benzyl bromide, 12.5 g (80%) of the expected compound of melting point 150°-151° C. were obtained. |
Here is a chemical reaction formula: Reactants are:m2:OC1=C(C(=O)OC)C=CC(=C1)I;m1:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)B(O)O)OCC2=CC=CC=C2, Reagents are:, and Products are 0:OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCC1=CC=CC=C1)C12CC3CC(CC(C1)C3)C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 7(f), by reacting 5.52 g (13.4 mmol) of 7-(1-adamantyl)-6-benzyloxy-2-naphthylboronic acid with 2.46 g (8.8 mmol) of methyl 2-hydroxy-4-iodobenzoate, 1.65 g (36%) of the expected compound was obtained. |
Here is a chemical reaction formula: Reactants are:m2:ICCCCCC;m1:OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)O)C12CC3CC(CC(C1)C3)C2, Reagents are:, and Products are 0:OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC(=C(C=C2C=C1)OCCCCCC)C12CC3CC(CC(C1)C3)C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 11, by reacting 430 mg (1 mmol) of methyl 2-hydroxy-4-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]benzoate with 180 μl (1.2 mmol) of 6-iodohexane, 280 mg (55%) of methyl 2-hydroxy-4-[7-(1-adamantyl)-6-hexyloxy-2-naphthyl]benzoate were obtained. |
Here is a chemical reaction formula: Reactants are:m1:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)O;m2:COCCOCCl, Reagents are:, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)C2=CC=C(C(=O)OC)C=C2)OCOCCOC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 12, by reacting 980 mg (2.4 mmol) of methyl 4-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]benzoate with 330 μl (28.6 mmol) of methoxyethoxymethyl chloride, 650 mg (55%) of the expected compound were obtained in the form of an oil. |
Here is a chemical reaction formula: Reactants are:m2:CC=1C=C(C(=O)OC)C=CC1I;m1:CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)B(O)O)C, Reagents are:, and Products are 0:CC=1C=C(C(=O)OC)C=CC1C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 7(f), by reacting 2.8 g (10 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.84 g (6.7 mmol) of methyl 3-methyl-4-iodobenzoate, 1.37 g (53%) of methyl 3-methyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained in the form of a yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:ICCC;m1:IC=1C=C(NC1)C(=O)OC, Reagents are:, and Products are 0:C(CC)N1C(=CC(=C1)I)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 7(d), by reacting 1.96 g (7.8 mmol) of methyl 4-iodo-2-pyrrolecarboxylate with 940 μl (9.6 mmol) of 3-iodopropane, 1.48 g (64%) of methyl N-propyl-4-iodo-2-pyrrolecarboxylate was obtained in the form of a slightly yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:C(CC)N1C(=CC(=C1)I)C(=O)OC;m1:CC1(C=2C=C3C=CC(=CC3=CC2C(CC1)(C)C)B(O)O)C, Reagents are:, and Products are 0:C(CC)N1C(=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 7(f), by reacting 1.7 g (6 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthrylboronic acid with 1.47 g (5 mmol) of methyl N-propyl-4-iodo-2-pyrrolecarboxylate, 450 mg (22%) of methyl N-propyl-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)-2-pyrrolecarboxylate were obtained. |
Here is a chemical reaction formula: Reactants are:m2:ICCC;m1:OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C, Reagents are:, and Products are 0:C(CC)OC1=C(C(=O)OC)C=CC(=C1)C1=CC2=CC=3C(CCC(C3C=C2C=C1)(C)C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 12, by reacting 2 g (5.1 mmol) of methyl 2-hydroxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate with 600 μl (6.1 mmol) of 3-iodopropane, 1.16 g (54%) of methyl 2-propyloxy-4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-anthryl)benzoate was obtained. |
Here is a chemical reaction formula: Reactants are:m1:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)O;m2:FC1=CC=C(CBr)C=C1, Reagents are:, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C2=C(C=C3C=CC(=CC3=C2)Br)OCC2=CC=C(C=C2)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the basic procedure of Example 11, by reacting 1.1 g (3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene with 420 μl (3,3 mmol) of 4-fluorobenzyl bromide, 1.2 g (86%) of the expected compound was obtained in the form of a colorless oil. |
Here is a chemical reaction formula: Reactants are:m3_m7:[H-].[Na+];m2:N[C@@H](CC1=CNC=N1)CO;m8_m4:Cl.Cl.N[C@@H](CC1=CNC=N1)CO;m5_m6:N1=CC=CC=C1;m5_m6:CC(C)(C)[Si](C)(C)Cl, Reagents are:m3_m7:CCCCCC;m8_m4:CN(C)C=O, and Products are 0:N.C(Cl)Cl;0:N[C@@H](CC1=CNC=N1)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: TBDMS protected histidinol 14--To a stirred solution of 205 mg (5.1 mmol) of NaH washed 3× with hexane, under argon, in 3.0 mL DMF was added in portions 500 mg (2.3 mmol) of histidinol dihydrochloride, resulting in moderate gas evolution. The solution was stirred for 1.5 h, then 1.8 mL (23 mmol) of anhydrous pyridine and 693.0 mg (4.6 mmol) of TBDMSCl was added. The solution was stirred for 1.5 h, concentrated in vacuo and flash chromatographed on silica with 15% CH3OH.NH3 /CH2Cl2 to yield 14. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(CCCO1)=O;m1_m2_m3:[Cl-].[NH4+];m1_m2_m3:NCC(C)(CN)CN, Reagents are:m0_m4:O, and Products are 0:NCC1(CN=C2N(C1)CCC2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 21.03 g (0.24 mol) of γ-butyrolactone and 1.31 g (24 mmol) of ammonium chloride in 114.5 g (0.98 mol) of 1,1,1-tris(aminomethyl)ethane was heated at 250° C. in an autoclave. After 1.5 h, the mixture was cooled and the excess amine and the water formed were removed by distillation. The residue was distilled at 200°-240° C./18 mbar. The yield was 22.0 g (54%) of yellowish oil. The boiling point was 117°-120° C./1 mbar. Other data concerning the product was: |
Here is a chemical reaction formula: Reactants are:m3:[H-].[Na+];m2:C(C(=O)OCC)(=O)OCC;m1:CC1=C(C(=CC(=C1)C)C)C(C)=O, Reagents are:m4:C1(=CC=CC=C1)C, and Products are 0:O=C(C(=O)OCC)CC(C1=C(C=C(C=C1C)C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2', 4', 6'-trimethylacetophenone (15 g, 92.6 mmol) and diethyl oxalate (20 g, 139 mmol) in 500 mL of anhydrous toluene was cautiously added 7.4 g of NaH (60% dispersion in mineral oil). The reaction mixture was slowly heated to reflux under N2. It was refluxed for about 20 minutes, then cooled, poured into ice-cold aqueous HCl solution, and extracted with ether. The extracts were washed with brine, dried over Na2SO4, filtered through a short silica gel pad and concentrated to give 16.2 g of a red oil which was used in the next reaction without further purification. |
Here is a chemical reaction formula: Reactants are:m1:O=C(C(=O)OCC)CC(C1=C(C=C(C=C1C)C)C)=O;m2_m3:Cl;m2_m3:N(=O)[O-].[Na+], Reagents are:m4:C(C)O, and Products are 0:O=C(C(=O)OCC)C(C(C1=C(C=C(C=C1C)C)C)=O)=NO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N2O3 gas was slowly passed into a stirred solution of the product of step A (16.2 g) in 300 mL of ethanol until the disappearance of starting material was confirmed by TLC. N2O3 gas was generated by the dropwise addition of 12N aqueous HCl solution into an aqueous slurry of NaNO2. The solvent was removed from the mixture and 200 mL of water was added to the residue. The product was then extracted into ether. The ether extract was dried over Na2SO4 and evaporated to give 16.1 g of a semi-solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:O=C(C(=O)OCC)C(C(C1=C(C=C(C=C1C)C)C)=O)=NO;m1_m2_m4_m3:Cl;m1_m2_m4_m3:CNN, Reagents are:m1_m2_m4_m3:CO, and Products are 0:NC=1C(=NN(C1C1=C(C=C(C=C1C)C)C)C)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of the product of step B (4.0 g, 13.8 mmol) and 1.6 mL of 12N hydrochloric acid in 100 mL of methanol was added dropwise 0.63 g of methyl hydrazine at 0° C. The reaction mixture was stirred at room temperature 4 hours, and then concentrated. The resulting residue was partitioned between water and ethyl acetate. The organic phase was separated and washed once with brine. The ethyl acetate solution was then mixed with 100 mL of water. Solid Na2S2O4 in excess was added in small portion until TLC showed completion of the reduction. The organic phase was separated, washed with water and brine, and dried over Na2SO4. Evaporation gave 3.1 g of the title compound as a foam. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(CC)NC=1C=2C(N=C(N1)C)=C(N(N2)C)C2=C(C=C(C=C2C)C)C;m1_m2_m3_m4:[OH-].[K+];m1_m2_m3_m4:BrCCC, Reagents are:m1_m2_m3_m4:CS(=O)C, and Products are 0:C(CC)N(C=1C=2C(N=C(N1)C)=C(N(N2)C)C2=C(C=C(C=C2C)C)C)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of the product of step F (400 mg, 1.2 mmol), powder KOH (1.0 g) and 1-bromopropane (1 mL) in 2 mL of DMSO was heated at 60° C. for 8 hours. The excess bromopropane was then evaporated. The mixture was partitioned between water and ether. The aqueous layer was separated and extracted with ether. The combined ether extracts were washed with water and brine, dried over Na2SO4 and concentrated to an oil. The oil was purified through silica gel column chromatography to give 260 mg of the title compound as an oil. 1H NMR (CDCl3): d 0.97 (t, 6H), 1.76 (m, 4H), 1.96 (s, 6H), 2.32 (s, 3H), 2.45 (s, 3H), 3.77 (s, 3H), 3.40-4.30 (br, 4H), 6.95 (s, 2H)ppm. The hydrochloride salt prepared in Ether/HCl melted at 210°-13° C. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:CC1=CC=C(C(=O)O)C=C1;m0_m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:CC1=CC=C(C(=O)Cl)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methylbenzoyl chloride was prepared in a conventional manner from 4-methylbenzoic acid and thionyl chloride and after excess thionyl chloride was distilled off, was used as the crude product in the side chain chlorination. |
Here is a chemical reaction formula: Reactants are:m1_m4:OCCC=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC;m3:[H][H];m2:[H][H], Reagents are:m1_m4:O1CCCC1;m5:[Pd], and Products are 0:OCCCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.38 g (1 mmol) of the thus obtained 2-(4-(4-hydroxy-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of tetrahydrofuran, added with 0.05 g of 10% Pd/C and subjected to a hydrogenation reaction in a hydrogen atmosphere under normal pressure. The reaction was stopped when about 25 ml of hydrogen was consumed. Then 10% Pd/C was filtered out and the filtrate was concentrated to obtain 0.38 g of 2-(4-(4-hydroxybutyl)-phenyl)-5-decyloxypyrimidine (yield: 99%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC;m1_m2_m3:C(C)O;m1_m2_m3:C(Cl)(Cl)Cl;m4:[BH4-].[Na+], Reagents are:m5:O, and Products are 0:OC(C)C1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 35.5 g (0.1 mo1) of 2-(4-acetylphenyl)-5-decyloxypyrimidine, 300 ml of ethanol and 300 ml of chloroform were supplied into a four-necked flask equipped with a stirrer and a thermometer. Then 2.8 g (0.075 mol) of sodium borohydride was added at 30°-40° C. and the mixture was stirred at the same temperature for 4 hours. The resulting reaction mixture was poured into 500 ml of water, followed by extraction and liquid separation, and the obtained chloroform layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 35.8 g of 2-(4-(1-hydroxyethyl) phenyl)-5-decyloxypyrimidine (II-c-11) (yield: 100%). |
Here is a chemical reaction formula: Reactants are:m1_m2:OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F, Reagents are:m3:[Ag]=O;m1_m2:C(CCC)I, and Products are 0:C(CCC)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 5 ml of butyl iodide. The solution was added with 3 g of silver oxide and stirred at 25°-30° C. for 4 days. The reaction mixture was cleared of silver oxide by filtration and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 0.98 g of (-)-2-(4-(3-butoxy-4,4,4-trifluoro-1-butenyl)phenyl)-5-decyloxypyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m3:OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F;m2:C(CCC)(=O)Cl, Reagents are:m4:C1(=CC=CC=C1)C;m1_m3:N1=CC=CC=C1, and Products are 0:C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of (-)-2-(4-(3-hydroxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine. The solution was added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order, and then the toluene layer was concentrated under reduced pressure. The residue was purified by subjecting it to silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.08 g of (+)-2-(4-(3-butyryloxy-4,4,4-trifluoro-1-butenyl) phenyl)-5-decyloxy-pyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m3:OC(CCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F;m2:C(CCCCCCCC)(=O)Cl, Reagents are:m1_m3:N1=CC=CC=C1;m4:C1(=CC=CC=C1)C, and Products are 0:C(CCCCCCCC)(=O)OC(CCCC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.1 g (2.5 mmol) of (-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine was dissolved in 10 ml of pyridine, followed by addition of 0.53 g (3 mmol) of nonanoyl chloride and 2-hour reaction at 20°-30° C. The reaction mixture was diluted with 100 ml of toluene, and the toluene layer was washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.25 g of (+)-2-(4-(4-nonanoyloxy-5,5,5-trifluoro-1-pentyl) phenyl-5-decyloxypyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m3:OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C;m2:C(CCC)(=O)Cl, Reagents are:m4:C1(=CC=CC=C1)C;m1_m3:N1=CC=CC=C1, and Products are 0:C(CCC)(=O)OC(C=CC1=CC=C(C=C1)C1=NC=C(C=N1)OCCCCCCCCCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of (-)-2-(4-(3-hydroxy-1-butenyl)phenyl)-5-decyloxypyrimidine was dissolved in 20 ml of pyridine, added with 0.5 g of butyryl chloride and stirred at 25°-30° C. for 4 hours. The reaction mixture was diluted with 100 ml of toluene and washed with 4N hydrochloric acid, water, a 5% sodium bicarbonate solution and water successively in that order. The toluene layer was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 1.05 g of (+)-2-(4-(3-butyryloxy-1-butenyl)phenyl)-5-decyloxy-pyrimidine. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)[O-].[Na+];m1_m4_m5:ClC1=NC(=NC(=C1)N)N;m3:[Cl-].ClC1=CC=C(C=C1)[N+]#N, Reagents are:m1_m4_m5:O;m1_m4_m5:C(C)(=O)O, and Products are 0:ClC1=C(C(=NC(=N1)N)N)N=NC1=CC=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 4-chloro-2,6-diaminopyrimidine (21.68 g, 0.150 mol) in water (750 ml) and acetic acid (750 ml) was added sodium acetate (300 g). Solution occurred after stirring for 20 minutes, and then the solution of 4-chlorobenzenediazonium chloride (0.166 mol) was added with cooling over 30 minutes at a rate that kept the reaction at 18°. The reaction was stirred overnight at room temperature, and the orange crystals were filtered, washed with water (4×400 ml), and dried in vacuo to give 17.6 g of 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidinediamine. The mother liquors were cooled to 5° for 20 hours, and the crystals were collected and dried in vacuo to give 6.94 g of additional 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidineadiamine. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC1=C(C(=NC(=N1)N)N)N=NC1=CC=C(C=C1)Cl, Reagents are:m5:[Zn];m1_m2_m3_m4:C(C)O;m1_m2_m3_m4:O;m1_m2_m3_m4:C(C)(=O)O, and Products are 0:ClC1=C(C(=NC(=N1)N)N)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 6-chloro-5-[(4-chlorophenyl)azo]-2,4-pyrimidinediamine (24.55 g, 0.0906 mol) in ethanol (640 ml), water (640 ml) and acetic acid (64 ml) was heated to 70° under nitrogen. Zinc dust (75 g) was added slowly over 1 hour, and then the reaction was stirred an additional hour at 70°. Then the reaction was cooled to room temperature and filtered under nitrogen. The filtrate was cooled to 0° and the pH was raised to 10 with 10% sodium hydroxide (400 ml). The precipitated zinc hydroxide was removed by filtration through Celite, and the dark red filtrate was neutralized to pH 7 with glacial acetic acid and concentrated to 300 ml. Water (50 ml) was added, the reaction was cooled to 0°, and the pH raised to 9 with 10% NaOH. The solution was allowed to stand at 5° for 3 days. The crystals were collected, washed with water (50 ml) and then ether (50 ml), and dried at 35° for 16 hours in vacuo to give 10.94 g of desired product. |
Here is a chemical reaction formula: Reactants are:m1_m2:N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1;m1_m2:ClCCCCC1=CNC2=CC=C(C=C12)C#N, Reagents are:, and Products are 0:C(#N)C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C=1C=CC2=C(C=C(O2)C(N)=O)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-(1-piperazinyl)benzofuran-2-carboxamide or a corresponding salt is reacted with 3-(4-chlorobutyl)-5-cyanoindole to give 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine and optionally then converted into its acid addition salt. |
Here is a chemical reaction formula: Reactants are:m1:[N+](=O)([O-])C=1C=CC2=C(C=C(O2)C(=O)OCC)C1, Reagents are:m3:[Ni];m2:CO, and Products are 0:NC=1C=CC2=C(C=C(O2)C(=O)OCC)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2.3 g of ethyl 5-nitrobenzofuran-2-carboxylate in 60 ml of methanol is hydrogenated in the presence of Raney nickel. The catalyst is filtered off and the solution is concentrated. After customary working up, ethyl 5-aminobenzofuran-2-carboxylate, Rf 0.1 (dichloromethane/ethanol 9.5:0.5) obtained; hydrochloride m.p. 246°-248°. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)OCC)C1;m1_m3_m2:C(C1=CC=CC=C1)Cl, Reagents are:m1_m3_m2:ClCCl, and Products are 0:C(C1=CC=CC=C1)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)OCC)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1 g of ethyl 5-(1-piperazinyl)-benzofuran-2-carboxylate in 50 ml of dichloromethane is treated with 1 g of benzyl chloride and stirred for 2 hours. After customary working up, ethyl 5-(4-benzyl-1-piperazinyl)benzofuran-2-carboxylate, m.p. 219°-222°, is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1, Reagents are:m1_m2:Cl, and Products are 0:N1(CCNCC1)C=1C=CC2=C(C=C(O2)C(=O)N)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1 g of 5-(4-tert-butoxycarbonyl-1-piperazinyl)-benzofuran-2-carboxamide is dissolved in 50 ml of methanolic HCl and stirred for I hour. After customary working up, 5-(1-piperazinyl)benzofuran-2-carboxamide, m.p. 252°-255°, is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:CN(NCCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C)C;m1_m2_m4_m3:OO;m1_m2_m4_m3:OO, Reagents are:m1_m2_m4_m3:CO, and Products are 0:CN(NCCCC[C@H]([NH+](C(=O)OCC1=CC=CC=C1)[O-])C(=O)OC(C)(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 25.3 g of dimethylamine 2, 7.9 mL of 30% hydrogen peroxide and 150 mL of methanol was stirred for 5 h after which an additional 7.9 g of 30% hydrogen peroxide was added. The reaction was allowed to stir for 48 h and monitored by silica gel TLC, eluting with solvent A. A 1 mL aqueous slurry of approximately 5 mg of platinum black was added whereupon the reaction was stirred for 7 h and another slurry of 5-10 mg platinum black added. The mixture was stirred overnight and monitored for peroxides using peroxide test paper with warming to 60° C. to remove peroxides when necessary. Once the reaction tested negative for peroxides, the mixture was filtered and concentrated. The residue was dissolved into 300 mL of EtOAc, dried over Na2SO4, filtered, concentrated and chromatographed on 400 g of silica gel, eluting with Solvent A to produce 13 g of product as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1:OC=1C=[N+](C=C(C1CC(C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1)CCC(C(=O)OCCCC)NC(=O)OCC1=CC=CC=C1)CCCCC(C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1;m2:Br, Reagents are:, and Products are 0:C1=C(C(=C(C=[N+]1CCCC[C@H](C(=O)[O-])N)O)C[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: reacting the pyridinium salt prepared in step (c) with HBr in an appropriate solvent to provide deoxypyridinoline. |
Here is a chemical reaction formula: Reactants are:m1_m5:C12C(CC3=CC=CC=C13)O2;m4:C(C)#N;m3:O;m2:CS(=O)(=O)O, Reagents are:m1_m5:C(Cl)Cl, and Products are 0:N[C@H]1[C@H](CC2=CC=CC=C12)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Indene oxide (117 g) diluted to a total volume of 600 mL in methylene chloride was diluted with acetonitrile (600 mL) and cooled to -20° C. Methanesulfonic acid (114 mL) was then added. The mixture was warmed to 25° C. and aged for 2 h. Water (600 mL) was added and the mixture heated at 45° C. for 5 h. The organic phase was separated and the aqueous phase further heated at reflux for 4 h with concentration to approximately 200 g/L. The solution was adjusted to pH 12.5 with 50% aqueous sodium hydroxide, and then cooled to 5° C. and filtered, dried in vacuo, to provide cis 1-amino-2-indanol. |
Here is a chemical reaction formula: Reactants are:m6_m0:C(C)#N;m2:S(O)(O)(=O)=O;m4:[OH-].[Na+];m3:O;m1_m5:[C@@H]1([C@@H](CC2=CC=CC=C12)O)O;m1_m5:C(C)#N, Reagents are:, and Products are 0:N[C@H]1[C@H](CC2=CC=CC=C12)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Trans-1,2-indandiol (1.5 g) was dissolved in acetonitrile (25 mL) cooled to 0° C., and concentrated sulfuric acid (1.1 mL) was added. The mixture was gradually warmed to 20° C. and aged to 3 hours. Water (2 mL) was added and the mixture heated to reflux. Concentrated aqueous sodium hydroxide was added to adjust the pH to 12. The resulting solid was removed by filtration to provide an aqueous acetonitrile solution of cis-1-amino-2-indanol (1.02 g, 63% yield). |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4:[C@@H]1([C@H](CC2=CC=CC=C12)O)O;m1_m4:C(C)#N;m2:S(O)(O)(=O)=O, Reagents are:, and Products are 0:N[C@H]1[C@H](CC2=CC=CC=C12)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Cis-1,2-indandiol (1.0 g) was dissolved in acetonitrile (20 mL), cooled to -40° C., and fuming sulfuric acid (21% SO3, 0.8 mL) was added. The mixture was aged for 1 hour with gradual warming to 0° C. Water was added and the mixture heated to 80° C. for 1 hour to provide an aqueous solution of cis-1-amino-2-indanol. |
Here is a chemical reaction formula: Reactants are:m3_m5:FC=1C=C(C=CC1F)Br;m4_m8:O;m1_m2:C(CC)C1CCC(CC1)C1=CC=C(C=C1)[Si](OC)(OC)OC;m1_m2:CCCC[N+](CCCC)(CCCC)CCCC.[F-], Reagents are:m3_m5:C1(=CC=CC=C1)C;m7_m6:C1(=CC=CC=C1)C;m7_m6:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1;m4_m8:C1(=CC=CC=C1)C, and Products are 0:C(CC)C1CCC(CC1)C1=CC=C(C=C1)C1=CC(=C(C=C1)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 0.645 g (2 mmol) of 4-(4-propylcyclohexyl)-phenyltrimethoxysilane (Ih) was added 2.1 ml of TBAF (2.1 mmol, 1M in THF) under nitrogen, and the mixture was stirred at room temperature for 30 minutes. After the solvent was removed under reduced pressure, a solution of 3,4-difluorobromobenzene (0.463 g, 2.4 mmol) in toluene (1 ml) was added, followed by the addition of a suspension of tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) in toluene (3 ml). The resulting mixture was refluxed for 3 hours. After cooling, to the reaction mixture were added water and toluene. The organic layer was separated and the aqueous layer was extracted with toluene three times. The combined organic layer was dried over magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane) to obtain 0.594 g (40%) of white crystals. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:N[C@H](C(=O)O)CCCCO;m1_m3_m2:Cl;m1_m3_m2:CO, Reagents are:, and Products are 0:Cl.N[C@H](C(=O)OC)CCCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of (S)-2-amino-6-hydroxyhexanoic acid (2.42 g., 16.4 mmole) in dry methanol (60 ml.) was treated with gaseous hydrogen chloride until the mixture began to reflux. The homogeneous solution was then stirred at room temperature for 2.5 hours. The solvent was stripped and the residue azeotroped three times with toluene to give crude (S)-2-amino-6-hydroxyhexanoic acid, methyl ester, hydrochloride salt as an oil. This oil was dissolved in dimethylformamide (20 ml.) and methylene chloride (50 ml.) and treated with 4-methyl morpholine (3.20 ml., 2.94 g., 29.1 mmole). This mixture was cooled to 0° C. and treated with (S)-2-phthalimido-4-pentenoic acid [obtained from 7.0 g., 16.4 mmole of the salt product from part (a) by partitioning between 10% potassium bisulfate and ethyl acetate] in methylene chloride (10 ml.), followed by solid hydroxybenzotriazole (2.22 g., 16.4 mmole) and ethyl-3-(3-dimethylamino)propyl carbodiimide, hydrochloride salt (3.458 g., 18.0 mmole). After stirring at 0° C. for 0.5 hour and at room temperature for 2 hours, the reaction was partitioned between ethyl acetate and 0.5N hydrochloric acid. The ethyl acetate extract was washed successively with water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped. The residue was flash chromatographed (Merck silica gel, ethyl acetate) to give pure title compound as an oil which solidified upon standing. The solid was triturated with ethyl ether and hexane and collected by filtration to give 5.149 g. of analytically pure title product; m.p. 90°-92° C.; [α]D =+25.6 (c=1.1, chloroform). TLC (ethyl acetate) Rf =0.36. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:[Br-].[K+];m1_m2_m4:N[C@H](CCCC)C(=O)O;m3:N(=O)[O-].[Na+], Reagents are:m1_m2_m4:S(O)(O)(=O)=O, and Products are 0:Br[C@H](C(=O)O)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Potassium bromide (15.9 g., .133 mmol.) was added to a stirred solution of D-norleucine (5.0 g., 38 mmol.) in 2.5N sulfuric acid (77 ml.) at room temperature. The reaction mixture was cooled to -10° C. and solid sodium nitrite (3.94 g., 57 mmol.) was added portionwise, maintaining the temperature between -10° and -5° C. After addition was complete, the foamy reaction was stirred for 1 hour and then warmed to room temperature and stirred for another hour. The reaction mixture was then extracted twice with ether, the ether extracts were washed once with water, dried (magnesium sulfate), filtered and evaporated to give 3.3 g. of crude title product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC(C(=O)O)=CC1=CC=CC=C1, Reagents are:m1_m2_m3:CO;m1_m2_m3:[Pd];m4:CO, and Products are 0:CC(C(=O)O)CC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of α-methyl cinnamic acid (10.0 g., 61.7 mmol.) in dry methanol (250 ml.) was treated with 10% palladium on carbon and hydrogenated (balloon used) at room temperature for 16 hours. The reaction mixture was diluted with methanol (250 ml.), filtered through a Celite pad in a millipore unit, washing the pad well with methanol (2×100 ml.). The clear filtrate was evaporated to dryness to give 10.225 g. of title product as a thick syrup. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C([O-])([O-])=O.[Cs+].[Cs+];m1_m2_m4_m3:C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O;m1_m2_m4_m3:C(C1=CC=CC=C1)Br, Reagents are:m1_m2_m4_m3:CN(C=O)C, and Products are 0:C1(C=2C(C(N1[C@H](C(=O)OCC1=CC=CC=C1)CCCCO)=O)=CC=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of cesium carbonate (3.819 g, 11.7 mmol.) and (S)-2-phthalimido-6-hydroxyhexanoic acid (6.00 g, 21.6 mmol.) in dimethylformamide (60 ml.) was treated with benzyl bromide (3.30 ml., 4.75 g., 27.7 mmol.). After stirring at room temperature for 2 hours, the mixture was partitioned between ethyl acetate and water. The organic extract was washed with water (twice) and brine, then dried (sodium sulfate), filtered and stripped to give an oil. The oil was flash chromatographed (Merck silica gel, 6/4-ethyl acetate/hexane) to give essentially pure product as a solid. Recrystallization from ethyl acetate/hexane gave 7.173 g. (1st crop) and 394 mg. (2nd crop) for a total of 7.567 g. of pure title product; m.p. 106°-108.5° C.; [α]D =-27-5° (c=1.5, methanol). TLC (75/25 ethyl acetate/hexanes) Rf =0.43. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C1(C=2C(C(N1[C@H](C(=O)O)CCCCO)=O)=CC=CC2)=O;m1_m2_m4_m3:C([O-])([O-])=O.[Cs+].[Cs+];m1_m2_m4_m3:CI, Reagents are:m5:C(C)(=O)OCC;m1_m2_m4_m3:CN(C=O)C, and Products are 0:C1(C=2C(C(N1[C@H](C(=O)OC)CCCCO)=O)=CC=CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give the title product as a colorless oil (3.825 g.). The oil was homogeneous by TLC (1:1-acetone:hexanes) Rf =0.37. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:CC(C)(OC(=O)N[C@@H]1C(N[C@@H](CCC1)C)=O)C;m1_m4_m2_m5:C[Si](C)(C)[N-][Si](C)(C)C.[Li+];m3:BrCC(=O)OCC, Reagents are:m1_m4_m2_m5:O1CCCC1;m1_m4_m2_m5:O1CCCC1, and Products are 0:CC(C)(OC(=O)N[C@@H]1C(N([C@@H](CCC1)C)CC(=O)OCC)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of (3S-cis)-hexahydro-3-[[(1,1-dimethylethoxy)carbonyl]amino]-7-methyl-2H-azepin-2-one [prepared as described in Example 64(f), 500 mg., 2.06 mmol.] in tetrahydrofuran (13 ml.) at room temperature under argon was treated dropwise with 1.0M lithium bis(trimethylsilyl)amide in tetrahydrofuran (2.7 ml., 2.7 mmol.) immediately followed by the dropwise addition of ethyl bromoacetate (0.47 ml., 4.21 mmol.). The resulting mixture was stirred for 30 minutes, quenched with aqueous ammonium chloride, diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered and concentrated to a yellow oil. Following flash chromatography (E Merck silica gel) eluting with 2:1 hexane/ethyl acetate, 750 mg. of title product was obtained as a light yellow oil; TLC (1:1 ethyl acetate:hexane) Rf =0.52. |
Here is a chemical reaction formula: Reactants are:m4_m7:C1(CCCC1)C(=O)O;m0_m2_m3_m6:C(C)(C)NC(C)C;m0_m2_m3_m6:C(CCC)[Li];m5_m8:BrCCCCCl, Reagents are:m4_m7:O1CCCC1;m0_m2_m3_m6:O1CCCC1;m5_m8:O1CCCC1, and Products are 0:C(C)(C)[N-]C(C)C.[Li+];0:ClCCCCC1(CCCC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of lithium diisopropylamide was prepared under nitrogen from diisopropylamine (31.0 ml., 220 mmol.) and n-butyl lithium (1.5M in hexane, 88.0 ml., 220 mmol.) in tetrahydrofuran (80 ml.), maintaining the temperature between -3° C. -1° C. After stirring 15 minutes, cyclopentanecarboxylic acid (11.4 g., 100 mmol.) in tetrahydrofuran (10 ml.) was added at 0° C.-3° C. over 25 minutes. After an additional 15 minutes at 0° C., the bath was removed and the reaction stirred 15 minutes more, causing the temperature to rise to 11° C. The milky white solution was cooled to -74° C. and 1-bromo-4-chlorobutane (23 ml., 200 mmol.) in tetrahydrofuran was added quickly, the temperature rising to -66° C. After 16 hours, the reaction was allowed to warm to room temperature in situ. The reaction was quenched with methanol (10 ml.) and concentrated in vacuo. The residue was partitioned between water (200 ml.) and ethyl ether (200 ml.). The aqueous layer was acidified to pH 1 with 12M hydrochloric acid and extracted with methylene chloride (3×150 ml.), dried (magnesium sulfate), filtered and evaporated to give 20.0 g. of the title product as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m3:C(C)N(CC)CC;m5:C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1;m4:C1(=CC=CC=C1)C(Cl)(C1=CC=CC=C1)C1=CC=CC=C1;m1_m2_m6:O.NN;m1_m2_m6:C1(C=2C(C(N1[C@H]1CCCC(NC1=O)(C)C)=O)=CC=CC2)=O, Reagents are:m1_m2_m6:CO, and Products are 0:C1(=CC=CC=C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)N[C@H]1CCCC(NC1=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Hydrazine monohydrate (4.59 ml., 94.6 mmol.) was added to a solution of (S)-hexahydro-6-phthalimido-2,2-dimethyl-2H-azepine-7-one [preparred as described in Example 66(e), 19.98 g., 68.76 mmol.] in methanol (250 ml.) at room temperature under argon. The resulting mixture was stirred for 72 hours then filtered to remove the white precipitate. The volatiles were evaporated and the residue was dissolved in methylene chloride (560 ml.) and filtered to remove additional precipitate. To this filtrate was added triethylamine (13.3 ml., 96.21 mmol.) followed by triphenylchloromethane (20.65 g., 74.07 mmol.) and the resulting mixture was stirred for 1.5 hours. Additional triphenylchloromethane (958 mg., 3.44 mmol.) was added and the solvent was removed. The residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried, filtered and concentrated to give a pale yellow foam. Following a crystallization from ethyl acetate and hexanes, 7.47 g. of title product was obtained as off-white crystals. The mother liquor was concentrated and crystallized from ethyl acetate and pentane to give a second crop (8.02 g.) of title product. The mother liquor was concentrated and the residue was flash chromatographed (E Merck silica gel) eluting with 4.5:5.5 ethyl acetate/hexanes to give 6.0 g of title compound as a white foam. The combined yield of title product was 21.49 g.; m.p. 139°-140° C.; [α]D =+43.4° (c=0.37, methylene chloride). TLC (2:3 hexane: ethyl acetate) Rf =0.63. |
Here is a chemical reaction formula: Reactants are:m1_m2:C=1(C(=CC=CC1)C=1C(=CC=CC1)O)O;m1_m2:P(Cl)(Cl)Cl, Reagents are:, and Products are 0:P1(OC2=C(C=CC=C2)C2=C(C=CC=C2)O1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2,2'-biphenol (28.1 g, 0.151 mol) in 49 mL phosphorus trichloride was heated at reflux for 2 hr. The excess PC13 was removed by distillation. The residue was purified by vacuum distillation (140°-143° C. at 0.5 mm Hg) to give 30.70 g (81% yield) 1,1'-biphenyl-2,2'-diyl phosphorochloridite (as a clear viscous oil which solidified to a White solid upon standing at room temperature (RT) in an inert atmosphere for an extended period of time). 31P{1H}NMR (121.4 MHz, d8 -toluene): δ180.1 (s), 85% H3PO4 external reference. |
Here is a chemical reaction formula: Reactants are:m1:[H][H];m4_m5:BrC=1C=C(C=CC1)CC(=O)OCC;m4_m5:BrC=1C=C(C=CC1)CC(=O)OCC;m6:[H-].C(C(C)C)[Al+]CC(C)C;m2_m3:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m2_m3:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, Reagents are:, and Products are 0:BrC=1C=C(C=CC1)CC=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In the preferred compounds of the invention the two R1 substituents are methyl, and the R2 and R3 substituents are hydrogen. Reaction Scheme 4 illustrates a synthetic process for preparing 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1-one (Compound G) which serves as a starting material for the synthesis of several preferred compounds of the invention. Thus, referring now specifically to Reaction Scheme 4, ethyl 3-bromophenylacetate (Compound B, made by esterification of 3-bromophenylacetic acid) is reduced with diisobutyl aluminum hydride (DIBAL H) to yield (3-bromophenyl)acetaldehyde. (3-Bromophenyl)acetaldehyde is reacted in a Wittig reaction with (carbethoxymethylene)triphenylphosphorane to provide a mixture of E and Z ethyl 4-(3-bromophenyl)but-2-enoates. The latter compounds are hydrogenated to yield ethyl 4-(3-bromophenyl)butanoate (Compound D). Compound D is reacted with the Grignard reagent derived from methylbromide to give the tertiary alcohol 5-(3-bromophenyl)-2-methylpentan-2-ol (Compound E) (It should be apparent to those skilled in the art, that the choice of the Grignard reagent used in this reaction step determines the nature of the R1 substituent in the resulting compounds of the invention.) Compound E is then treated with acid to cyclize it and to form 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F). Compound F is in the scope of Formula 17, and in accordance with Reaction Schemes 2 and 3 serves as the starting material in the synthesis of several preferred compounds of the invention. Compound F is oxidized with chromium trioxide to yield 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G). Compound G is covered by Formula 10 and in accordance with Reaction Scheme 1 serves as a starting material in the synthesis of several preferred compounds of the invention. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrC1=CC=C(C=C1)CC(=O)OCC;m1_m2_m3:BrC1=CC=C(C=C1)CC(=O)OCC;m1_m2_m3:BrC=1C=C(C=CC1)CC(=O)O, Reagents are:, and Products are 0:BrC=1C=C(C=CC1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl (4-bromophenyl)acetate (Compound A), 100 g (463 mmol) of 3-bromophenylacetic acid was converted into the title compound (yellow oil) using 2 g of conc. H2SO4 and 500 ml of ethanol. |
Here is a chemical reaction formula: Reactants are:m4:[H-].C(C(C)C)[Al+]CC(C)C;m1_m2_m5_m3:BrC1=CC=C(C=C1)CC(=O)OCC;m1_m2_m5_m3:BrC1=CC=C(C=C1)CC(=O)OCC;m1_m2_m5_m3:[H-].C(C(C)C)[Al+]CC(C)C, Reagents are:m1_m2_m5_m3:C(Cl)Cl, and Products are 0:BrC1=CC=C(C=C1)CC=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl (4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an additional hour. The reaction was quenched by the dropwise addition of methanol (10 ml), followed by water (10 ml) and 10% HCl (40 ml). The mixture was then warmed to 0° C., stirred for 10 minutes and then washed with water (15 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgSO4 and the solvent distilled off at ambient temperature to give crude (4-bromophenyl)acetaldehyde. To a cold solution (0° C.) of this crude aldehyde in 150 ml of CH2 Cl2 was added a solution of 26 g (74.6 mmol) of (carbethoxy methylene)triphenylphosphorane in 50 ml of CH2Cl2. The mixture was stirred for 16 hours, concentrated in vacuo and purified by flash chromatography (silica, 10% EtOAc-hexane) to give ethyl 4-(4-bromophenyl)but-2-enoate as a mixture of E:Z isomers. This isomeric mixture was dissolved in 150 ml of EtOAc and hydrogenated over 1 g of 10% Pd/C for 6 hours. The catalyst was filtered off and the filtrate concentrated in vacuo to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC1=CC=C(C=C1)CC=O;m1_m2_m3_m4:ClCl;m1_m2_m3_m4:C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m1_m2_m3_m4:C(Cl)Cl, and Products are 0:BrC1=CC=C(C=C1)CC=CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl (4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an additional hour. The reaction was quenched by the dropwise addition of methanol (10 ml), followed by water (10 ml) and 10% HCl (40 ml). The mixture was then warmed to 0° C., stirred for 10 minutes and then washed with water (15 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgSO4 and the solvent distilled off at ambient temperature to give crude (4-bromophenyl)acetaldehyde. To a cold solution (0° C.) of this crude aldehyde in 150 ml of CH2 Cl2 was added a solution of 26 g (74.6 mmol) of (carbethoxy methylene)triphenylphosphorane in 50 ml of CH2Cl2. The mixture was stirred for 16 hours, concentrated in vacuo and purified by flash chromatography (silica, 10% EtOAc-hexane) to give ethyl 4-(4-bromophenyl)but-2-enoate as a mixture of E:Z isomers. This isomeric mixture was dissolved in 150 ml of EtOAc and hydrogenated over 1 g of 10% Pd/C for 6 hours. The catalyst was filtered off and the filtrate concentrated in vacuo to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC1=CC=C(C=C1)CCCC(=O)OCC;m1_m2_m3_m4:BrC1=CC=C(C=C1)CCCC(=O)OCC;m1_m2_m3_m4:BrC=1C=C(C=CC1)CC(=O)OCC;m1_m2_m3_m4:BrC=1C=C(C=CC1)CC(=O)OCC, Reagents are:, and Products are 0:BrC=1C=C(C=CC1)CCCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing the same general multistep preparation as for ethyl 4-(4-bromophenyl)butanoate (Compound C), 60 g (246 mmol) of ethyl (3-bromophenyl)acetate (Compound B) was converted into the title compound (oil) using 255 ml (255 mmol) of diisobutyl aluminum hydride (DIBAL-H, 1M in hexane), 85.8 g (250 mmol) of (carbethoxy methylene)triphenylphosphorane and 1.7 g of 10% Pd/C. |