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Here is a chemical reaction formula: Reactants are:m1_m2:CN;m1_m2:N1=CC(=CC=C1)C#CCCO, Reagents are:m3:O, and Products are 0:CNCCC#CC=1C=NC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: An aqueous methylamine solution (5 mL, 40%, 58.7 mmole) was mixed with XII (200 mg, 0.08 mmole) and stirred for 3 hr. in a sealed tube at 45° C. After the reaction was complete, water (10 mL) was added to the cooled reaction mixture, and the reaction mixture was extracted with chloroform (10×5 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated. The residue obtained was chromatographed on a silica gel column using methanol:chloroform (1:9) and then with a chloroform: methanol mixture containing 1% triethylamine as eluent. About 70 mg of XIII was obtained as a slightly yellow syrup, which was distilled at 110°-112° C., 0.04 mm Hg. XIII was converted to its mono fumarate salt form, which exhibits a melting point of 103°-104° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m3:BrCC1=CC=C(C#N)C=C1;m1_m5_m2:[H-].[Na+];m1_m5_m2:N1C(NCC1)=O, Reagents are:m1_m5_m2:CN(C=O)C, and Products are 0:O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was filtered to give 4,4'-[(2-oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NC(=O)N;m3_m1_m2:CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C, Reagents are:m3_m1_m2:C(C)(=O)O, and Products are 0:CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl)-2,3dihydro-5-phenyl-1H-imidazol-2-one; NMR (CDCl3) 10.98 (s,2), 7.5 (m,4), 7.4 (m,5), 3.18 (s,6) ppm. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m2_m3_m4:BrCC=1C=C(C#N)C=CC1;m1_m2_m3_m4:[H-].[Na+], Reagents are:m1_m2_m3_m4:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, 2 mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chromatography on silica; NMR (DMSO-d6) 11.02 (s,1), 7.4 (m,4), 7.3 (m,2), 7.2 (m,7), 4.75 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m3_m7:BrCC=1C=C(C(=O)OC)C=CC1;m4:Cl;m1_m5_m2_m6:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m5_m2_m6:[H-].[Na+], Reagents are:m3_m7:CN(C)C=O;m1_m5_m2_m6:CN(C)C=O;m1_m5_m2_m6:CN(C)C=O, and Products are 0:COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DMF was then added and the reaction stirred for 10 min at 50° C. The mixture was poured into 1N HCl, filtered, washed with water and dried. Chromatography on silica gel (2% EtOH in 7:3 methylene chloride/ethyl acetate) afforded 1.2 g of 3-(3-methoxycarbonylphenyl)methyl-4,5-diphenyl-1H-imidazol-2-one as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:BrCC1=CC=C2C=CC(=CC2=C1)C#N;m1:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s,1), 7.9 (d,1), 7.85 (d,1), 7.55 (m,3), 7.4 (m,2), 7.2 (m,9), 7.0 (m,3), 5.1 (s,2), 4.95 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m1_m5:N1CCOCC1.OC=1C=C(C(=O)O)C=CC1[N+](=O)[O-];m2:[H-].[Na+];m3_m6:C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)CBr)(C1=CC=CC=C1)C1=CC=CC=C1;m4:O, Reagents are:m1_m5:CN(C=O)C;m3_m6:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The compound ([3]-(32)-587) (0.99 g) prepared in Example 36 was dissolved in dry N,N-dimethylformamide (19 ml), and 50% sodium hydride (0.20 g) was added to the solution. The mixture was stirred at room temperature for 15 minutes. A solution of N-(triphenylmethyl)-5-[4'-(bromomethyl)biphenyl-2-yl]tetrazole (2.19 g) in N,N-dimethylformamide (6.5 ml) was added to the solution. The mixture was stirred at room temperature for 39 hours. The reaction mixture was added to water (50 ml), and extracted with chloroform (100 ml). The organic layer was washed, dried over anhydrous sodium sulfate, and concentrated to obtain the compound (2.72 g) as a light yellow solid. The product was purified by silica gel column chromatography (Kieselgel 60=190 g, chloroform/ethyl acetate=7/3) to obtain the compound ([3]-(33)-587) (1.41 g) |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1[N+](=O)[O-])(C1=CC=CC=C1)C1=CC=CC=C1;m1_m2_m5:C(C)O;m4_m3:O.NN, Reagents are:m1_m2_m5:C(C)(=O)OCC;m4_m3:[Pd], and Products are 0:C1(=CC=CC=C1)C(N1N=NN=C1C1=C(C=CC=C1)C1=CC=C(C=C1)COC=1C=C(C(=O)N2CCOCC2)C=CC1N)(C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of the compound ([3]-(33)-587) (0.60 g) prepared in Example 37, ethanol (150 ml), and ethyl acetate (40 ml) was stirred at 70° C. for 15 minutes. After 10% Pd/C (0.10 g) and hydrazine monohydrate (1 ml) were added to the solution, the mixture was stirred at 70° C. for 1 hour. The insolubles were filtered through celite, and the filtrate was concentrated to obtain colorless foam (0.67 g). The product was purified by silica gel column chromatography (Kieselgel 60=80 g, chloroform/ethyl acetate=13/7) to obtain the compound ([3]-(34)-587) (0.09 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5_m4:NC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-];m1_m2_m3_m5_m4:ON1N=NC2=C1C=CC=C2;m1_m2_m3_m5_m4:C1(CCCCC1)N=C=NC1CCCCC1;m1_m2_m3_m5_m4:N1CCOCC1, Reagents are:m1_m2_m3_m5_m4:CN(C=O)C, and Products are 0:NC1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-amino-3-nitrobenzoic acid (7.40 g), 1-hydroxybenzotriazole (6.59 g), dicyclohexylcarbodiimide (10.90 g), dry N,N-dimethylformamide (74 ml), and morpholine (4.3 ml) was stirred at room temperature for 2 hours. The insolubles were filtered out, and washed with N,N-dimethylformamide. The filtrate and the washing were combined, and concentrated to obtain a yellowish brown solid (16.01 g). |
Here is a chemical reaction formula: Reactants are:m2:O.NN;m1_m3:C(CCCCC)C1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-], Reagents are:m1_m3:C(C)O;m5_m4:C(C)O;m5_m4:[Pd], and Products are 0:NC=1C=C(C(=O)N2CCOCC2)C=CC1CCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The compound ([5]-(54)-75) (700 mg) prepared in Example 62 was dissolved in ethanol (35 ml). After the solution was heated to 50° C., a suspension of 10% Pd/C (70 mg) in ethanol was added, and hydrazine monohydrate (0.35 ml) was added to the solution. The solution was stirred at 50° C. for 30 minutes. After the reaction was completed, the solution was filtered through celite 545 to remove the catalyst. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate) to obtain the above-captioned compound ([5]-(55)-75) (631 mg) as colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m5:CC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-];m2_m3_m7_m4:ON1N=NC2=C1C=CC=C2;m2_m3_m7_m4:Cl.C(C)N=C=NCCCN(C)C;m2_m3_m7_m4:N1CCOCC1, Reagents are:m1_m5:CN(C)C=O;m6:O;m2_m3_m7_m4:C(C)N(CC)CC, and Products are 0:CC1=C(C=C(C(=O)N2CCOCC2)C=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The compound ([5]-(53)-278) (6.5272 g) prepared in Example 72 was dissolved in anhydrous DMF (98 ml). Then, 1-hydroxybenzotriazole (6.3297 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.9795 g), triethylamine (6.5 ml), and morpholine (4.1 ml) were added to the solution. The mixture was stirred at room temperature for 4 hours. A small amount of water was added to the resulting yellowish orange solution including the white salt to obtain a homogeneous solution. The solution was concentrated. The residue was dissolved in chloroform, and the solution was washed with 1N HCl aqueous solution and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown crystals (8.9903 g). The product was recrystallized from n-hexane/ethyl acetate to obtain the above-captioned compound ([5]-(54)-278) (7.8455 g) as light yellow crystals. |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:ON1N=NC2=C1C=CC=C2;m2_m3_m4:Cl.C(C)N=C=NCCCN(C)C;m2_m3_m4:N1CCOCC1;m5_m6_m1:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1, Reagents are:m5_m6_m1:O1CCCC1;m5_m6_m1:ClCCl;m7:C(Cl)(Cl)Cl, and Products are 0:[N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In tetrahydrofuran (100 ml) and dichloromethane (100 ml), 3-nitrobenzoic acid (7.58 g) was dissolved. Then 1-hydroxybenzotriazole (6.74 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (9.57 g), and morpholine (9.47 g) were added to the solution. The mixture was stirred at room temperature overnight. After the reaction was completed, chloroform was added to the solution. The mixture was washed with 1N-HCl aqueous solution, 1N-NaOH aqueous solution, and distilled water. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=160 g, ethyl acetate) to obtain the above-captioned compound ([13]-(132)-158) (9.62 g) as white crystals. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C(=O)N2CCOCC2)C=CC1, Reagents are:m5_m3_m4:C(C)O;m5_m3_m4:O.NN;m5_m3_m4:[Pd];m1_m2:C(C)O, and Products are 0:NC=1C=C(C(=O)N2CCOCC2)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The compound ([13]-(132)-158) (8.63 g) prepared in Example 83 was dissolved in ethanol (400 ml), and the solution was heated to 50° C. To the suspention, a solution of 10% Pd/C (2.25 g) in ethanol and hydrazine monohydrate (4.4 ml) were added to the solution. The mixture was stirred for 30 minutes. After the reaction was completed, the catalyst was removed by filtration through celite. The solution was concentrated, and the residue was purified by silica gel column chromatography (Kieselgel 60=120 g, ethyl acetate) to obtain the above-captioned compound ([13]-(133)-158) (7.57 g) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ON1N=NC2=C1C=CC=C2;m1_m2_m3:C1(CCCCC1)N=C=NC1CCCCC1;m1_m2_m3:N1CCOCC1;m4:CN(C=O)C, Reagents are:, and Products are 0:C(CCCC)(=O)NC=1C=C(C(=O)N2CCOCC2)C=CN1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The compound ([9]-(94)-467') (2.4610 g) prepared in Example 98 was dissolved in anhydrous dimethylformamide (DMF) (37 ml). Then, 1-hydroxybenzotriazole (1.9477 g), N,N'-dicyclohexylcarbodiimide (2.9739 g), and morpholine (1.3 ml) were added to the solution. The mixture was stirred at room temperature for 16 hours. The insolubles were filtered out, and the filtrate was concentrated. The resulting residue was dissolved in chloroform, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain yellowish brown oil (7.4981 g). The crude oil was purified by silica gel column chromatography (Kieselgel 60=230 g, chloroform/acetone=5/1) to obtain the above-captioned compound ([9]-(94)-467") (3.1756 g) as white crystals. |
Here is a chemical reaction formula: Reactants are:m2:CO[C@@H](C(=O)O)C;m4:CO[C@@H](CO)C;m3:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:, and Products are 0:CO[C@H](CO)C;0:CO[C@H](C(=O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By reduction of the (+)-(R)-2-methoxy-propionic acid known from the prior art with lithium aluminium hydride (LiAlH4) the (-)-(R)-2-methoxy-propanol is obtained with a boiling point of 70° C. under a pressure of 76 mbar and a specific rotation of [α]D25 =-15.8° (c=100). The corresponding (+)-(S)-2-methoxy-propanol with a boiling point of 70° C. under a pressure of 76 mbar and a rotation of [α]D25 =+16.5° (c=100) is obtained analogously from the equally well known (-)-(S)-2-methoxy-propionic acid. |
Here is a chemical reaction formula: Reactants are:m2:C1(=CC=C(C=C1)S(=O)(=O)Cl)C;m1:CO[C@@H](CO)C, Reagents are:m3:N1=CC=CC=C1, and Products are 0:CO[C@@H](COS(=O)(=O)C1=CC=C(C=C1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By reacting (-)-(R)-2-methoxypropanol with p-toluenesulphonic acid chloride in pyridine analogously to R. S. Tipson [J. Org. Chem. 9 (1944) 235] the (+)-(R)-2-methoxypropyl-p-toluenesulphonate is obtained in the form of a yellowish oil with a specific rotation of [α]D25 =+3.7° (c=100) and analogously, from (+)-(S)-2-methoxy-propanol, the corresponding (-)-(S)-2-methoxypropyl-p-toluenesulphonate is obtained with a rotation of [α]D25 =-3.7° (c=100). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m6_m3_m4:C(#C)C1(CN2CCC1CC2)O;m1_m2_m5_m6_m3_m4:BrC=1C=CC(=NC1)OCCCC;m1_m2_m5_m6_m3_m4:C(C)N(CC)CC, Reagents are:m1_m2_m5_m6_m3_m4:CN(C=O)C;m1_m2_m5_m6_m3_m4:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl;m1_m2_m5_m6_m3_m4:[Cu]I, and Products are 0:C(CCC)OC1=CC=C(C=N1)C#CC1(CN2CCC1CC2)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of 3-ethynyl-3-hydroxyquinuclidine (600 mg), 5-bromo-2-n-butoxypyridine (920 mg), bis-(triphenylphosphine)-palladium (II) chloride (140 mg), copper (I) iodide (70 mg) and dry triethylamine (10 ml) in dry dimethylformamide (20 ml) was heated at 90° C. under an atmosphere of argon for 6 hours. The reaction mixture was cooled and the dimethylformamide and triethylamine were removed by evaporation. The residue was treated with 2M aqueous sodium hydroxide solution (20 ml) and the resulting mixture extracted with dichloromethane (3×20 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give a brown residue which was crystallised from acetonitrile to yield 3-[2-(6-butoxy-3-pyridyl)ethynyl]quinuclidin-3-ol (300 mg) as a solid, m.p. 149°-151° C.; microanalysis, found: C, 71.3; H, 7.9; N, 8.9%; C18H24N2O2 0.1H 2O requires: C, 71.47; H, 8.08; N, 9.26%; NMR (DHSOd6): 0.9-1.0(3H, t), 1.2-1.35(1H, m), 1.35-1.5(2H, m), 1.5-1.65(1H, m), 1.65-1.75(2H, m), 1.75-2.0(3H, m), 2.6-2.75(4H, t), 2.8-2.85(1H, d), 3.02-3.17(1H, d), 4.2-4.3(2H, t), 5.55(1H, s), 6.75-6.83(1H, d), 7.65-7.72(1H, d) and 8.2(1H, s); m/Z 301 (M+H). |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[Na+];m1_m4:C(CCC)O;m3:BrC1=NC=C(C=C1)Br;m2:[H][H], Reagents are:, and Products are 0:BrC=1C=CC(=NC1)OCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sodium hydride (60% w/v dispersion in mineral oil; 1.8 g) was added in portions over 20 minutes to n-butanol (100 ml) with stirring. The mixture was then stirred until no further hydrogen evolution was noted. 2,5-Dibromopyridine (7.1 g) was added and the resulting mixture stirred at reflux for 6 hours. After cooling, the n-butanal was removed by evaporation and the residue was treated with water (50 ml) and extracted with dichloromethane (2×20 ml). The organic extracts were combined, washed with water (20 ml), dried (MgSO4) and evaporated to give 5-bromo-2-n-butoxypyridine (6.3) as a pale yellow oil, NMR (DHSOd6): 0.9-0.96(3H, t), 1.32-1.5(2H, m), 1.62-1.76(2H, m), 4.2-4.28(2H, t), 6.79-6.82(1H, d), 7.85-7.9(1H, d of d) and 8.26(1H, d). |
Here is a chemical reaction formula: Reactants are:m4:Cl.CN(CCCN=C=NCC)C;m1_m2_m3_m5:C(=O)(OC(C)(C)C)[C@H](C(C(=O)O)(N)N)C;m1_m2_m3_m5:C(C)N(CC)CC;m1_m2_m3_m5:O.ON1N=NC2=C1C=CC=C2, Reagents are:m1_m2_m3_m5:C1CCOC1, and Products are 0:C(C)(C)(C)OC(N[C@@H]1C(NCC1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: (S)-Boc-Diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and 1-hydroxybenzotriazole hydrate (19.3 g, 143 mmol) are dissolved in 300 mL of THF. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol) is added to the solution. The solution is heated at 60° C. over 15 min. A white precipitate forms and the solution is kept at 60° C. for 4 h. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CC(=CC=C1)C#N)=O)=O;m1_m3_m2:Cl, Reagents are:m1_m3_m2:CCOC(=O)C, and Products are 0:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (9.1 g, 29 mmol) in 150 mL of EtOAc at 0° C. is bubbled HCl gas for 10 min. After this time, the solution is stirred for 4 h. The solution is then concentrated to afford the title compound (7.3 g, 29 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m3:C(C)N(CC)CC;m1_m4_m2:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O;m1_m4_m2:S1C2=C(C=C1S(=O)(=O)Cl)C=CC=C2, Reagents are:m5:CCOC(=O)C;m1_m4_m2:C(Cl)Cl, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride (0.36 g, 1.43 mmol) in 15 mL of CH2Cl2 is added benzo[b]thiophene-2-sulfonyl chloride (0.32 g, 1.38 mmol). To the resulting solution is added triethylamine (0.29 g, 2.88 mmol). After 16 h, the solution is diluted with EtOAc. The solution is washed with 1N HCl, saturated NaHCO3, and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The title compound (0.45 g, 1.09 mmol) is obtained as white solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=CC1;m1_m4_m2:CI;m3:C(=O)([O-])[O-].[K+].[K+], Reagents are:m1_m4_m2:CN(C)C=O;m5_m6:O;m5_m6:CCOC(=O)C, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)N(S(=O)(=O)C2=CC3=C(S2)C=CC=C3)C)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of benzo[b]thiophene-2-sulfonic acid [1-(3-cyano-benzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.61 mmol) in 3 mL of DMF is added methyl iodide (0.13 g, 0.91 mmol) followed by K2CO3 (0.13 g, 0.91 mmol). The solution is stirred at ambient temperatures for 6 h. After this time, the solution is diluted with H2O and EtOAc. The layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is triturated with Et2O to give the title compound (0.25 g, 0.59 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:OCC=1C=C(SC1)C#N;m1_m4_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m4_m2_m3:C(Br)(Br)(Br)Br, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:BrCC=1C=C(SC1)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4-hydroxymethyl-thiophene-2-carbonitrile (10 g, 72 mmol), in 360 mL of THF is added triphenyl phosphine (18.3 g, 76 mmol) and carbon tetrabromide (25 g, 76 mmol). After 3 h, the solution is filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to afford the title compound (14 g, 69 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m2_m3:BrCC=1C=C(SC1)C#N;m2_m3:[H-].[Na+];m1:C(C)(C)(C)OC(N[C@@H]1C(NCC1)=O)=O, Reagents are:m4:C1CCOC1.CN(C)C=O, and Products are 0:C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CSC(=C1)C#N)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (2-oxo-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester (3.2 g, 16 mmol), prepared as described in EXAMPLE 1, Part A in 80 mL of THF:DMF (10:1) at 0° C. is added 4-bromomethyl-thiophene-2-carbonitrile (3.23 g, 16 mmol) and sodium hydride (60% dispersion in oil, 0.67 g, 16.8 mmol). After addition, the solution was allowed to warm to ambient temperatures. After 2 h, the solution is quenched by the addition of sat. NH4Cl. The solution is diluted with H2O and EtOAc. The layers are separated. The organic layer is washed with H2O and sat. NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with gradient of 20% EtOAc/CH2 Cl2 to 30% EtOAc/CH2Cl2 to afford the title compound (4.0 g, 13.8 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(C)(C)OC(N[C@@H]1C(N(CC1)CC1=CSC(=C1)C#N)=O)=O;m1_m3_m2:Cl, Reagents are:m1_m3_m2:CCOC(=O)C, and Products are 0:Cl.N[C@@H]1C(N(CC1)CC=1C=C(SC1)C#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: [1-(5-Cyanothiophene3-ylmethyl)-2-oxo-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (4.0 g, 13.8 mmol) is added to a solution of 100 mL of EtOAc saturated with HCl gas at 0° C. After 3 h, the solution is concentrated. The title compound (3.3 g, 13.5 mmol) is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are:m1:FC(C(=O)O)(F)F.ClC1=CC(=CC=2SC(=CC21)S(=O)(=O)N[C@@H]2C(N(CC2)CC=2C=C(C(=N)N)C=CC2)=O)Cl;m4_m2:CN1CCCCC1;m3:ClC(=O)OCC(Cl)(Cl)Cl, Reagents are:m5:CCOC(=O)C;m4_m2:C(Cl)Cl.CN(C)C=O, and Products are 0:ClC(COC(NC(=N)C1=CC(=CC=C1)CN1C([C@H](CC1)NS(=O)(=O)C1=CC2=C(S1)C=C(C=C2Cl)Cl)=O)=O)(Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-[3-(S)-(4,6-dichlorobenzo[b]thiophene-2-sulfonylamino)-2-oxo-pyrrolidin-1-ylmethyl]-benzamidine trifluoroacetate (0.25 g, 0.40 mmol), prepared as in EXAMPLE 14, Part E, in 4 mL of CH2Cl2 :DMF (10:1) is added N-methyl piperidine (0.12 g, 1.2 mmol) followed by trichloroethyl chloroformate (0.93 g, 0.44 mmol). The solution is stirred for 16 h. After this time, the solution is diluted with EtOAc. The organic layer is washed with 1N HCl, H2O, saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (0.20 g, 0.30 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:NC1=C(C=C(C#N)C=C1)C;m1_m4_m2_m3:C(C1=CC=CC=C1)(=O)C1=CC=CC=C1;m1_m4_m2_m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m4_m2_m3:C1(=CC=CC=C1)C, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4-amino-3-methyl benzonitrile (1.20 g, 9.08 mmol) in 75 mL of toluene is added benzophenone (1.74 g, 9.53 mmol) and p-toluenesulfonic acid (0.43 g, 2.1 mmol). The reaction vessel is fitted with a Dean-Stark trap and the solution is heated at reflux. After 24 h, the solution is cooled to ambient temperatures. The solution is concentrated. The crude material is purified by column chromatography eluting with a gradient of 3% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (2.43 g, 8.2 mmol) is obtained as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)C;m1_m4_m2_m3:BrN1C(CCC1=O)=O;m1_m4_m2_m3:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, Reagents are:m1_m4_m2_m3:C(Cl)(Cl)(Cl)Cl;m5:C(Cl)Cl, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=C(C=C(C#N)C=C1)CBr, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4-(benzhydrylidene-amino)-3-methyl-benzonitrile (1.36 g, 4.27 mmol) in 40 mL of CCl4 is added N-bromosuccinimide (0.84 g, 4.7 mmol) and benzoyl peroxide (0.22 g, 0.64 mmol). The solution is heated to reflux for 16 h. The solution is cooled to ambient temperatures. The solution is diluted with CH2Cl2. The solution is washed with 1N NaOH and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes. The title compound (0.91 g, 2.43 mmol) is obtained as an oil. |
Here is a chemical reaction formula: Reactants are:m4:S(=O)([O-])[O-].[Na+].[Na+];m1_m2_m3_m5:C(C=1C(O)=CC=CC1)=O;m1_m2_m3_m5:ClCl;m1_m2_m3_m5:ICl, Reagents are:m6:C(Cl)Cl;m1_m2_m3_m5:C(Cl)Cl, and Products are 0:OC1=C(C=O)C=C(C=C1)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of salicylaldehyde (10 g, 82 mmol) in 50 mL of CH2 Cl2 is added 22 mL of a 1M ICl solution in CH2Cl2. The solution is stirred for 14 h. After this time, a saturated solution of sodium sulfite is added until the color is discharged. The solution is diluted with CH2Cl2. The layers are separated. The organic layer is washed with water. The organic layer is dried over MgSO4, filtered and concentrated. The resulting crude material is recrystallized from cyclohexane to give the title compound (7.2 g, 32 mmol) as white solid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:Cl.NC1C(N(CC1)CC=1C=C(C#N)C=CC1O)=O;m1_m3_m2:ClC1=CC(=CC=2SC(=CC21)S(=O)(=O)Cl)Cl, Reagents are:m1_m3_m2:N1=CC=CC=C1, and Products are 0:OC1=C(CN2C(C(CC2)NS(=O)(=O)C2=CC3=C(S2)C=C(C=C3Cl)Cl)=O)C=C(C=C1)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride (0.20 g, 0.75 mmol) in 3 mL of pyridine at 0° C. is added 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The solution is allowed to warm to ambient temperatures and is stirred for 6 h. After this time, the solution is concentrated. The residue is dissolved in CH2 Cl2. The organic solution is washed with 1N HCl and saturated NaCl. The crude product is triturated with Et2O to give the title compound (0.22 g, 0.44 mmol) as a white solid. |
Here is a chemical reaction formula: Reactants are:m5_m8:C(CCC)N(CCCC)CCCC;m4_m7:[N-]=[N+]=[N-].[Na+];m1_m6_m2:S1C(=CC=C1)C=CC(=O)O;m1_m6_m2:C(C)N(CC)CC;m3:ClC(=O)OCC, Reagents are:m10:O;m5_m8:C1(=CC=CC=C1)OC1=CC=CC=C1;m4_m7:O;m1_m6_m2:CC(=O)C, and Products are 0:S1C=CC=2C(NC=CC21)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-thiophene-2-yl-acrylic acid (7.39 g, 47.9 mmol) in 200 mL of acetone is added triethylamine (4.9 g, 47.9 mmol). The resulting solution is cooled to 0° C. and ethyl chloroformate (5.7 g, 52.8 mmol) is added dropwise. After 2 h, sodium azide (4.67 g, 71.9 mmol) in 25 mL of H2O is then added. The solution is stirred for 1.5 h at 0° C. After this time, the solution is poured into 300 mL of H2O. A white precipitate forms which is collected by filtration. The resulting solid is dried over P2O5 under vacuum. The solid is suspended in 20 mL of diphenyl ether. This solution is added dropwise to a solution of tributylamine (6.9 g, 37.4 mmol) in 200 ml of diphenyl ether at 190° C. After 2 h, the solution is cooled to ambient temperatures. The solution is diluted with 1000 mL of hexanes and is cooled to 0° C. The resulting solid is collected by filtration and the solid is washed with hexanes. The title compound (3.6 g, 23.8 mmol) is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2:S1C=CC=2C(NC=CC21)=O;m1_m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:ClC1=NC=CC2=C1C=CS2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5H-Thieno[3,2-c]pyridin-4-one (1.0 g, 6.62 mmol) is dissolved in 30 mL of phosphorous oxy chloride. The solution is heated to 100° C. After 4 h, the solution is concentrated. The residue is dissolved in CH2 Cl2. The resulting solution is washed with water and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 40% CH2Cl2 /hexanes to 60% CH2Cl2 /hexanes. The title compound (1.0 g, 5.8 mmol) is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl;m0_m1:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2sulfonyl chloride. The product is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are:m4:CCOC(=O)C;m1_m5:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=CC1;m2_m3:CI;m2_m3:[H-].[Na+], Reagents are:m1_m5:CN(C)C=O, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)N(S(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)C)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.56 mmol) is dissolved in 6 mL of DMF and cooled to 0° C. To the solution is added methyl iodide (0.40 g, 2.82 mmol) and sodium hydride (25 mg of a 60% dispersion in mineral oil, 0.62 mmol). The reaction mixture is allowed to warm to room temperature and is stirred for 2 h. At this time, the solution is diluted with and EtOAc and the layers are separated. The organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated to give the title compound (0.25 g, 0.54 mmol) as a solid. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=CC=C2C(=N1)SC(=C2)S(=O)(=O)Cl;m0_m1:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC=3C(=NC(=CC3)Cl)S2)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 6-chlorothieno[2,3-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/CH2 Cl2 to 25% EtOAc/CH2Cl2 to afford a white solid. |
Here is a chemical reaction formula: Reactants are:m0_m1:Cl.OC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O;m2:ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl, Reagents are:, and Products are 0:C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 4-hydroxy-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 17, Part F using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The product is obtained as a white solid. |
Here is a chemical reaction formula: Reactants are:m0_m1:Cl.Cl.NC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O;m2:ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl, Reagents are:, and Products are 0:NC1=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=NC(=CC=C3S2)Cl)=O)C=C(C=C1)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 4-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile dihydrochloride as described in EXAMPLE 17, Part F using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/CH2Cl2 to 25% EtOAc/CH2Cl2 to afford a white solid. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=CC=C2C(=N1)C=C(S2)S(=O)(=O)Cl;m0_m1:Cl.N[C@@H]1C(N(CC1)CC=1C=C(SC1)C#N)=O, Reagents are:, and Products are 0:C(#N)C1=CC(=CS1)CN1C([C@H](CC1)NS(=O)(=O)C1=CC2=NC(=CC=C2S1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 4-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-thiophene-2carbonitrile hydrochloride as described in EXAMPLE 1, Part E using 5-chlorothieno[3,2-b]pyridine-2-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The product is triturated with Et2O/CH2Cl2 /hexanes to give a white solid. |
Here is a chemical reaction formula: Reactants are:m2_m3:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)S(=O)(=O)C)=O)C=CC1;m1:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)S(=O)C)=O)C=CC1, Reagents are:m2_m3:CCO, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C2=NC(=NC=C2)N)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of [5-(2-methylsulfinyl-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin3-(S)-yl]-amide and [5-(2-methylsulfonyl-pyrimidin-4-yl)-thiophene-2sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.20 g, 0.39 mmol) is dissolved in 10 mL of EtOH and NH3 gas is bubbled through the solution for 5 min. The resulting mixture is heated at 90° C. for 3 h in a stainless steel Parr high pressure reaction vessel. After this time, the solution is allowed to cool to room temperature and is concentrated in vacuo to give [5-(2-amino-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.20 g) as a crude product. FAB MS, [M+H]+ =455. The crude [5-(2-amino-pyrimidin-4-yl)-thiophene-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide is converted to the title compound as described in EXAMPLE 1, Part F. The crude product is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 60% CH3CN/H2O (0.1% TFA) and the appropriate product fractions are lyophilized to provide the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=CC=C(S1)C=1SC(=CC1)S(=O)(=O)Cl;m0_m1:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC=C(S2)C=2SC(=CC2)Cl)=O)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-benzonitrile hydrochloride as described in EXAMPLE 1, Part E using 5'-chloro-[2,2']bithiophenyl-5-sulfonyl chloride in place of benzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with EtOAc/CH2Cl2 to yield a beige solid. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2_m3:Cl.Cl.NC1=C(C=C(C#N)C=C1)CN1C([C@H](CC1)N)=O;m0_m1_m2_m3:S1C2=C(C=C1S(=O)(=O)Cl)C=CC=C2;m0_m1_m2_m3:C(C)#N, Reagents are:, and Products are 0:NC1=C(C=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=CC=C3)=O)C=C1)C#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound (0.131 g, 0.307 mmol) is prepared as in EXAMPLE 1, Part E from 4-amino-3-(3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)benzonitrile dihydrochloride (0.135 g, 0.445 mmol) and benzo[b]thiophene-2-sulfonyl chloride (0.114 g, 0.49 mmol) in acetonitrile. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:N1C=NC=C1;m1_m2_m3_m4:C(C)(C)(C)[Si](Cl)(C)C;m1_m2_m3_m4:C(#N)C=1C=CC(=C(CN2C(C(CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C1)O, Reagents are:m5:CCOC(=O)C;m1_m2_m3_m4:CN(C)C=O, and Products are 0:C(C)(C)(C)[Si](OC1=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C=C(C=C1)C#N)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Imidazole (0.094 g, 1.37 mmol) and t-butyldimethylchlorosilane (0.099 g, 0.66 mmol) are added to a solution of 5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide (0.25 g, 0.55 mmol) in 10 mL of DMF. The resulting mixture is stirred overnight, then diluted with EtOAc and washed with saturated NaHCO3 (aq) and brine. The organic layer is dried over MgSO4, filtered and concentrated. The product is purified by column chromatography eluting with 3% MeOH/CH2Cl2 to give a brown oil (0.236 g, 0.41 mmol). |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:ClC=1C=NC=C(C1)Cl;m0_m1_m2:S1C(=CC=C1)B(O)O, Reagents are:, and Products are 0:ClC=1C=C(C=NC1)C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound (0.21 g, 1.08 mmol) was prepared from 3,5-dichloropyridine (1.0 g, 6.76 mmol) and 2-thiophene boronic acid (0.95 g, 7.43 mmol) as described in EXAMPLE 48, Part B. |
Here is a chemical reaction formula: Reactants are:m3:BrC=1C=NC=CC1;m2:ClC1=CSC=C1;m1:ClC1=C(SC=C1)B(O)O, Reagents are:, and Products are 0:ClC1=C(SC=C1)C1=NC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Chlorothiophene-2-boronic acid (1.5 g, 9.24 mmol), prepared as described in EXAMPLE 48, Part A from 3-chlorothiophene was reacted with 3-bromopyridine (0.81 mL, 8.4 mmol) as described in EXAMPLE 48, Part B to give the title compound (0.232 g, 1.19 mmol). |
Here is a chemical reaction formula: Reactants are:m2:ClC=1C=CC2=C(SC(=C2)S(=O)(=O)Cl)C1;m1:Cl.NC1C(N(CC1)CC=1C=C(C#N)C=CC1O)=O, Reagents are:, and Products are 0:C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C2=CC3=C(S2)C=C(C=C3)Cl)=O)C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 3-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-hydroxy-benzonitrile hydrochloride as described in EXAMPLE 17, Part G substituting 6-chlorobenzo[b]thiophene-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with Et2O to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m5:BrC=1C=C(C=O)C=CC1;m1_m2_m4_m5:C(CC(=O)O)(=O)O;m3:Cl, Reagents are:m1_m2_m4_m5:N1CCCCC1;m1_m2_m4_m5:N1=CC=CC=C1, and Products are 0:BrC=1C=C(C=CC1)C=CC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Bromobenzaldehyde (10.0 g, 54 mmol), malonic acid (10.1 g, 97 mmol) and piperidine (0.267 mL, 2.7 mmol) are treated with pyridine (30 mL) and heated at 100° C. for 3.5 h. The reaction mixture is cooled to room temperature, poured into 200 ml of 20% hydrochloric acid at 0° C.; the resultant precipitate is collected, washed with copious amounts of water and dried in a vacuum dessicator overnight to afford the title compound (11.64 g, 51 mmol). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:BrC=1C=CC(=C(C=O)C1)F;m1_m3_m2:[BH4-].[Na+], Reagents are:m1_m3_m2:C1CCOC1, and Products are 0:BrC=1C=CC(=C(CO)C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5-bromo-2-fluoro-benzaldehyde (6.10 g, 30.0 mmol) in 30 mL of THF at 0° C. is added 5 mL of sodium borohydride (2.0M solution in triglyme, 10.0 mmol). The reaction mixture is stirred at 0° C. for 25 min and then quenched by the addition of 1N HCl. The mixture is diluted with EtOAc and the layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with 15% EtOAc/hexanes to afford the title compound (6.00 g, 29.3 mmol). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:BrC=1C=CC(=C(CO)C1)F;m1_m4_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m3:BrN1C(CCC1=O)=O, Reagents are:m1_m4_m2:C1CCOC1, and Products are 0:BrC=1C=CC(=C(CBr)C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5-bromo-2-fluoro-benzyl alcohol (3.10 g, 15.1 mmol) in 30 mL of THF at 10° C. is added triphenyl phosphine (4.10 g, 15.6 mmol) followed by N-bromosuccinimide (2.67 g, 15.0 mmol). The ice bath is removed and the resulting solution is stirred for 20 min at room temperature. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to give the title compound (3.90 g, 14.5 mmol). |
Here is a chemical reaction formula: Reactants are:m1:Cl.N[C@@H]1C(N(CC1)CC=1C=C(C#N)C=CC1F)=O;m2:N1=CC(=CC=C1)C1=CC=C(S1)S(=O)(=O)Cl, Reagents are:, and Products are 0:C(#N)C=1C=CC(=C(CN2C([C@H](CC2)NS(=O)(=O)C=2SC(=CC2)C=2C=NC=CC2)=O)C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 3-(S)-[(3-amino-2-oxo-pyrrolidin-1-yl)-methyl]-4-fluoro-benzonitrile hydrochloride as described in EXAMPLE 17, Part G substituting 5-pyridin-3-yl-thiophene-2-sulfonyl chloride in place of 4,6-dichlorobenzo[b]thiophene-2-sulfonyl chloride. The crude product is triturated with Et2O to give the title compound as a white solid |
Here is a chemical reaction formula: Reactants are:m0_m2_m3:BrC1=CC=C(N)C=C1;m0_m2_m3:C(C=CC1=CC=CC=C1)(=O)Cl, Reagents are:, and Products are 0:ClC1=NC2=CC=C(C=C2C=C1)Br;0:BrC=1C=C2C=CC(NC2=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound is prepared from 4-bromoaniline and cinnamoyl chloride according to the procedure described in J. Chem. Soc., Perkin Trans. I, 1972, 1648. The crude 6-bromo-1H-quinolin-2-one intermediate obtained is triturated in Et2O/hexanes and filtered to give a beige solid which is used directly in the chlorination step. The crude product is recrystallized in MeOH to afford the title compound as a beige solid. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:Cl.COC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)OC)C1;m1_m5_m2:B(Cl)(Cl)Cl;m3_m4:C(C)O;m3_m4:CO, Reagents are:m1_m5_m2:ClCCCl, and Products are 0:ClCCCl.Cl.OC=1C=CC2=C(SC(=C2C(C2=CC=C(C=C2)OCCN2CCCCC2)=O)C2=CC=C(C=C2)O)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 6-methoxy-2-(4-methoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene hydrochloride (2.0 g) in 1,2-dichloroethane (20 mL) was treated with boron trichloride (2.0 mL). The resulting mixture was stirred at 35° C. for about 18 hours. A mixture of ethanol and methanol (10 mL, 95:5, 3A) was treated with the reaction mixture from above, causing the alcoholic mixture to reflux. Upon complete addition, the resulting crystalline slurry was stirred at 25° C. After one hour, the crystalline product was filtered, washed with cold ethanol (10 mL), and dried at 40° C. in vacuo to give 1.78 g of the title compound. The X-ray powder diffraction pattern is identical to that reported in Table 1. Melting point 255° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:OC1(CC[N+]2(CCCC2)CC1)C1=CC=CC=C1;m1_m2_m3_m4:ClC=1C=NNC1;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m5:C(C)OCC;m1_m2_m3_m4:CN(C=O)C, and Products are 0:ClC=1C=NN(C1)CCCCN1CCC(CC1)(C1=CC=CC=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 15.0 g (48 mmol) of 8-hydroxy-8-phenyl-5-azoniaspiro[4,5]decane, 5.4 g (53 mmol) of 4-chloropyrazole and 13.2 g of potassium carbonate in 200 ml of dimethylformamide is heated at reflux for 20 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform and washing is carried out repeatedly with water. The organic phase is dried with anhydrous sodium sulfate and evaporation is carried out at reduced pressure, a crude product being obtained which is suspended in ethyl ether, which is filtered while cold and which is washed with ethyl ether. 12.4 g (37.1 mmol) of 4-chloro-1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl]-1H-pyrazole are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(=CC=CC=C1)C=1CCNCC1;m1_m2_m3_m4:ClCCCCN1C=CC2=CC=CC=C12;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m4:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1C=CC2=CC=CC=C12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.8 g (30 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine, 6.22 g of 1-(4-chlorobutyl)indole and 8.3 g of potassium carbonate in 100 ml of dimethylformamide is heated at 90° C. for 3 hours. Evaporation to dryness is then carried out at reduced pressure, the residue is redissolved in chloroform and washing is carried out repeatedly with water. The organic phase is dried with anhydrous sodium sulfate and evaporation is carried out at reduced pressure, a crude product being obtained which is purified by chromatography on silica gel. 5.7 g (17.3 mmol). of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]indole are obtained. |
Here is a chemical reaction formula: Reactants are:m3_m6:ClCCCN1CCC(=CC1)C1=CC=CC=C1;m1_m4_m2_m5:ClC=1C=NNC1;m1_m4_m2_m5:[H-].[Na+], Reagents are:m3_m6:CN(C=O)C;m1_m4_m2_m5:CN(C=O)C;m1_m4_m2_m5:CN(C=O)C, and Products are 0:ClC=1C=NN(C1)CCCN1CCC(=CC1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2.05 g (20 mmol of 4-chloropyrazole in dimethylformamide is added dropwise to a suspension of 1.0 g of NaH in dimethylformamide. The white suspension is heated for 30 minutes at 100° C. Cooling is carried out and 4.7 g (20 mmol) of 1-(3-chloropropyl)-4-phenyl-1,2,3,6-tetrahydropyridine, dissolved in dimethylformamide, are added. Heating is carried out at reflux for 2 hours. Evaporation to dryness is then carried out and the residue is extracted with chloroform, washed with water and dried with sodium sulfate. The resulting crude product is purified by chromatography on silica gel. 5.2 g (17.2 mmol) of 4-chloro-1-[3-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)propyl]-1H-pyrazole are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1(CCN(CC1)CCCCN1C=NC2=C1C=CC=C2)C2=CC=CC=C2;m1_m2_m3:Cl, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1C=NC2=C1C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 13.4 g (38.2 mmol) of 1-[4-(4-hydroxy-4-phenyl-1-piperidyl)butyl]-1H-benzimidazole, 150 ml of concentrated HCl and 75 ml of ethanol is heated at reflux for 6 hours. The ethanol is then evaporated and the aqueous solution is cooled, basified with dilute NaOH and extracted with chloroform. The organic phase is dried with anhydrous sodium sulfate and evaporated at reduced pressure, a crude product being obtained which is purified by chromatography on silica gel. 9.1 g (27.5 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-benzimidazole are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:[H-].[H-].[H-].[H-].[Li+].[Al+3];m1_m2_m3:C1(=CC=CC=C1)C=1CCN(CC1)CC(CCN1N=CC=C1)=O, Reagents are:m1_m2_m3:C1CCOC1, and Products are 0:C1(=CC=CC=C1)C=1CCN(CC1)CCCCN1N=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.0 g of LiAlH4 are added to a solution of 3.3 g (10 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-3-oxobutyl]-1H-pyrazole in 25 ml of THF. The resulting mixture is refluxed for 2 hours. The excess LiAlH4 is destroyed by addition of concentrated NaOH and water. The inorganic salts are filtered off and the THF is evaporated under vacuum, giving 2.6 g (8.2 mmol) of 1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-pyrazole. |
Here is a chemical reaction formula: Reactants are:m1:Cl.C(C)O;m2_m3:ClC=1N=C(N(C1Cl)CCCCN1CCC(=CC1)C1=CC=CC=C1)C, Reagents are:m2_m3:C(C)O, and Products are 0:Cl.ClC=1N=C(N(C1Cl)CCCCN1CCC(=CC1)C1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.5 ml of an 8.4N hydrochloric acid/ethanol solution are added to a solution, cooled in an ice bath, of 7.4 g (20.3 mmol) of 4,5-dichloro-2-methyl-1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)butyl]-1H-imidazole in 15 ml of absolute ethanol. After a few minutes, a precipitate appears which is filtered, washed with cold ethanol and dried, 7.7 g (19.2 mmol) of 4,5-dichloro-2-methyl-1-[4-(4-phenyl-1,2,3,6-tetrahydro-1-pyridyl)-butyl]-1H-imidazole hydrochloride being obtained. |
Here is a chemical reaction formula: Reactants are:m4:C(O)([O-])=O.[Na+];m1_m2_m5:CC=1N=COC1C(=O)Cl;m1_m2_m5:Cl.CNOC;m3:N1=CC=CC=C1, Reagents are:m1_m2_m5:C(Cl)(Cl)Cl, and Products are 0:CON(C(=O)C1=C(N=CO1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methyl-5-oxazolecarbonyl chloride (15 g) and N,O-dimethylhydroxylamine hydrochloride (11 g) in dry chloroform (100 ml) were cooled to 0° C. and dry pyridine (28.5 g) was added. The mixture was allowed to warm to room temperature. After 30 minutes aqueous sodium hydrogen carbonate was added and the organic layer separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed, dried and evaporated. The residue was purified by flash chromatography to yield the title compound as a white solid. M.p. 59°-60° C. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[Na+];m3_m6:CON(C(=O)C1=C(N=CO1)C)C;m2:C(CCC)[Li];m1_m5:BrC1=COC=C1, Reagents are:m3_m6:C(C)OCC;m7:C(C)O;m1_m5:C(C)OCC, and Products are 0:CC=1N=COC1C(=O)C1=COC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Bromofuran (2.5 g) in dry diethylether was stirred and cooled to -70° C. under an atmosphere of dry nitrogen and n-butyllithium (2.5M solution in hexane, 6.8 ml) was added dropwise. After 30 minutes, N-methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (2.89 g) in dry diethylether was added dropwise. After a further 30 minutes the mixture was allowed to warm to room temperature. Ethanol (5 ml) was added followed by saturated aqueous sodium chloride. The mixture was extracted with dichloromethane and the material thus obtained was purified by flash chromatography to give the title compound. M.p. 82°-83.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(CCC)[Li];m1_m2_m4:CC=1N=CSC1;m3:C[Si](C)(C)Cl, Reagents are:m1_m2_m4:C(C)OCC, and Products are 0:CC=1N=C(SC1)[Si](C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Butyllithium (2.5M solution in hexane, 1.1 equivalents) was added dropwise to a solution of 4-methylthiazole (1.0 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, trimethylsilylchloride (1.0 equivalent) was added dropwise. The mixture was allowed to warm to room temperature and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. Work-up in the normal fashion and vacuum distillation then gave the title compound. B.p. 42° C. at 1 mmHg. |
Here is a chemical reaction formula: Reactants are:m1:CON(C(=O)C1=C(N=C(O1)C)C)C;m2:C(C)(C)(C)[Li], Reagents are:, and Products are 0:CC=1OC(=C(N1)C)C(=O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with N-methoxy-N-methyl-2,4-dimethyl-5-oxazolecarboxamide and t-butyllithium and following the general method of Preparation 3, the title compound was prepared. |
Here is a chemical reaction formula: Reactants are:m3:FC(C(=O)OCC)(F)F;m4:Cl;m1_m2_m5:BrC1=COC=C1;m1_m2_m5:C(CCC)[Li], Reagents are:m1_m2_m5:C(C)OCC, and Products are 0:FC(C(=O)C1=COC=C1)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Bromofuran (20 g) was added to a solution of n-butyllithium (2.5M in hexanes, 60 ml) in diethyl ether (200 ml) at -70° C. After 30 minutes, ethyl trifluoroacetate (28.6 g) was added slowly. After a further 1 hour the mixture was allowed to warm to room temperature and was then left to stir overnight. 1M Hydrochloric acid (100 ml) was added and the mixture stirred for 5 minutes. The organic layer was separated, washed, dried and evaporated. The residue was distilled to give the title compound. B.p. 118° C. |
Here is a chemical reaction formula: Reactants are:m3:NC(=S)N;m1_m2_m4:OC=1C(=C(C=CC1)I)OS(=O)(=O)C1=CC=C(C)C=C1;m1_m2_m4:FC(C(CC(C)=O)=O)(F)F, Reagents are:m1_m2_m4:C(C)#N, and Products are 0:C(C)(=O)C1=C(N=C(S1)N)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Hydroxy(tosyloxy)iodobenzene (78.5 g) was added to a solution of 1,1,1-trifluoropentane-2,4-dione in acetonitrile (500 ml). The mixture was heated under reflux for 45 minutes, then cooled, and thiourea (15.2 g) was added. The mixture was heated under reflux for 4 hours and then left to stand overnight. Evaporation and crystallisation of the residue from dichloromethane gave the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m6_m2_m7:BrC=1C(=NNC1C)C;m1_m6_m2_m7:[H-].[Na+];m5:C(O)([O-])=O.[Na+];m4:IC;m3:[H][H], Reagents are:m1_m6_m2_m7:CN(C=O)C;m1_m6_m2_m7:CN(C=O)C, and Products are 0:BrC=1C(=NN(C1C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Bromo-3,5-dimethylpyrazole (10 g) in dry dimethylformamide (50 ml) was added to a stirred suspension of sodium hydride (1.8 g) in dry dimethylformamide at 0° C. When the evolution of hydrogen was complete, iodomethane (8.9 g) was added dropwise. The mixture was allowed to warm to room temperature and after 30 minutes saturated aqueous sodium hydrogen carbonate (5 ml) was added. Following evaporation under high vacuum, the residue was purified by column chromatography to give the title compound. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m2_m4:FC(C(=O)N1C=NC=C1)(F)F;m1_m2_m4:CC=1N=C(OC1)[Si](C)(C)C, Reagents are:m1_m2_m4:C(C)OCC, and Products are 0:CC=1N=C(OC1)C(C(F)(F)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Trifluoroacetylimidazole (10 g) was added dropwise to 4-methyl-2-trimethylsilyloxazole (J. Chem. Soc., Chem. Commun., 1984, 258) (9.95 g) in diethyl ether (100 ml) at 0° C. under an atmosphere of dry nitrogen. The mixture was stirred overnight at room temperature. Water was added and the organic layer was separated, washed, dried and evaporated. Flash chromatography gave the title compound. |
Here is a chemical reaction formula: Reactants are:m3_m7:C(C)(=O)C1=C(N=CO1)C;m4:O;m1_m5_m2_m6:BrC1=CSC=C1;m1_m5_m2_m6:C(CCC)[Li], Reagents are:m3_m7:C(C)OCC;m1_m5_m2_m6:C(C)OCC;m1_m5_m2_m6:C(C)OCC, and Products are 0:CC=1N=COC1C(C)(O)C1=CSC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Bromothiophene (4.23 g) in diethylether (10 ml) was added dropwise to n-butyllithium (2.5M solution in hexane, 10.4 ml) in dry diethylether (20 ml) at -70° C. under a nitrogen atmosphere. After 3 hours 5-acetyl-4-methyloxazole (2.5 g) in diethylether (10 ml) was added dropwise. After a further 2.5 hours at -70° C., the mixture was allowed to warm to room temperature and then left overnight. The mixture was poured into water and extracted with ether. The product thus obtained was crystallised from diethylether to give 1-(4-methyl-5-oxazolyl)-1-(3-thienyl)ethanol, m.p. 87°-89° C. |
Here is a chemical reaction formula: Reactants are:m2:C(CCC)[Li];m1_m5:S1C=CC=C1;m4:C(O)([O-])=O.[Na+];m3_m6:C(C)(=O)C1=C(N=CO1)C, Reagents are:m1_m5:O1CCCC1;m3_m6:O1CCCC1, and Products are 0:CC=1N=COC1C(C)(O)C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Thiophene (3.36 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to -40° C. under a dry nitrogen atmosphere and n-butyllithium (2.5M solution in hexane, 16 ml) was added dropwise. The mixture was allowed to warm to -20° C. and then after 1 hour was cooled to -70° C. 5-Acetyl-4-methyloxazole (5 g) in dry tetrahydrofuran (15 ml) was added dropwise. After a further 1 hour the mixture was allowed to warm the room temperature and was stirred for a further 2 hours. Aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The material thus obtained was purified by flash chromatography to give the title compound. M.p. 84°-85° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)C1=C(N=C(O1)C)C;m1:BrC1=CSC=C1, Reagents are:, and Products are 0:CC=1OC(=C(N1)C)C(C)(O)C1=CSC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromothiophene and 5-acetyl-2,4-dimethyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 132°-133° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)C1=C(N=C(O1)CC)C;m1:BrC1=CSC=C1, Reagents are:, and Products are 0:C(C)C=1OC(=C(N1)C)C(C)(O)C1=CSC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromothiophene and 5-acetyl-2-ethyl-4-methyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 77.5°-79° C. |
Here is a chemical reaction formula: Reactants are:m1:BrC1=COC=C1;m2:CC=1N=COC1C(CC)=O, Reagents are:, and Products are 0:O1C=C(C=C1)C(CC)(O)C1=C(N=CO1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromofuran and 4-methyl-5-propionyloxazole and following the general method of Example 4 the title compound was prepared. |
Here is a chemical reaction formula: Reactants are:m1:BrC1=COC=C1;m2:C(C)(=O)C1=C(N=C(O1)CC)C, Reagents are:, and Products are 0:C(C)C=1OC(=C(N1)C)C(C)(O)C1=COC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromofuran and 5-acetyl-2-ethyl-4-methyloxazole and following the general method of Example 4 the title compound was prepared. |
Here is a chemical reaction formula: Reactants are:m1:BrC1=CSC=C1;m2:CC=1OC(=C(N1)C)C(CC)=O, Reagents are:, and Products are 0:CC=1OC(=C(N1)C)C(CC)(O)C1=CSC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromothiophene and 2,4-dimethyl-5-propionyloxazole and following the general method of Example 4 the title compound was prepared. Purification by preparative HPLC gave a white solid. M.p. 81°-83° C. |
Here is a chemical reaction formula: Reactants are:m1:BrC1=COC=C1;m2:C(C)(=O)C=1N=C(OC1C)C, Reagents are:, and Products are 0:CC=1OC(=C(N1)C(C)(O)C1=COC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromofuran and 4-acetyl-2,5-dimethyloxazole and following the general method of Example 4 the title compound was prepared. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)C=1N=C(OC1C)C;m1:BrC1=CSC=C1, Reagents are:, and Products are 0:CC=1OC(=C(N1)C(C)(O)C1=CSC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 3-bromothiophene and 4-acetyl-2,5-dimethyloxazole and following the general method of Example 4 the title compound was prepared. M.p. 83°-84° C. |
Here is a chemical reaction formula: Reactants are:m4:C(CCC)[Li];m5:C(C)(=O)C1=C(OC(=C1)C)C;m2:C(CCC)[Li];m3:C[Si](C)(C)Cl;m6:C(O)([O-])=O.[Na+];m1_m7:CC=1N=CSC1, Reagents are:m1_m7:O1CCCC1, and Products are 0:CC=1OC(=CC1C(C)(O)C1=C(N=CS1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)C=1OC=CC1;m1:CC=1N=CSC1, Reagents are:, and Products are 0:O1C(=CC=C1)C(C)(O)C1=C(N=CS1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 4-methylthiazole and 2-acetylfuran and following the general method of Example 15 the title compound was prepared. M.p. 127°-128° C. |
Here is a chemical reaction formula: Reactants are:m1:CC=1N=CSC1;m2:C(C)(=O)C=1SC=CC1, Reagents are:, and Products are 0:CC=1N=CSC1C(C)(O)C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Starting with 4-methylthiazole and 2-acetylthiophene and following the general method of Example 15 the title compound was prepared. M.p. 146.5°-147.5° C. |
Here is a chemical reaction formula: Reactants are:m2_m6:C[Si](C=1SC=CN1)(C)C;m3_m7:C(C)(=O)C1=CSC=C1;m1_m5:C(CCC)[Li];m4:C(O)([O-])=O.[Na+], Reagents are:m2_m6:C(C)OCC;m3_m7:C(C)OCC;m1_m5:C(C)OCC, and Products are 0:S1C=NC=C1C(C)(O)C1=CSC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Butyllithium (2.5M solution in hexane, 5.6 ml) in diethylether (25 ml) was stirred at -70° C. under a nitrogen atmosphere and 2-trimethylsilylthiazole (2 g) in diethylether (25 ml) was added dropwise. After 30 minutes 3-acetylthiophene (1.93 g) in diethylether (25 ml) was added dropwise. After a further 45 minutes the mixture was allowed to warm to room temperature and then left to stir for a further 1 hour. Saturated aqueous sodium hydrogen carbonate was added and the organic layer was separated. The aqueous layer was extracted with diethylether. The organic layers were combined, washed, dried and evaporated and the residue was purified by flash chromatography to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m4:C(O)([O-])=O.[Na+];m1_m5_m2_m3:O1C=C(C=C1)C(C)(O)C1=C(N=CO1)C;m1_m5_m2_m3:Cl;m1_m5_m2_m3:C(C)OCC, Reagents are:m1_m5_m2_m3:C(Cl)(Cl)Cl, and Products are 0:O1C=C(C=C1)C(=C)C1=C(N=CO1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol (900 mg) in dry chloroform was treated with 1M anhydrous hydrogen chloride in diethylether (1.1 equivalents). After 10 minutes at room temperature, aqueous sodium hydrogen carbonate was added and the mixture was extracted with dichloromethane. The material thus obtained was purified by flash chromatography to give the title compound as an almost colourless liquid. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:CC=1OC(=C(N1)C)C(C)(OC)C1=COC=C1;m1_m3_m2_m4:Cl, Reagents are:m1_m3_m2_m4:C(C)OCC;m1_m3_m2_m4:C(C)OCC, and Products are 0:Cl.CC=1OC(=C(N1)C)C(=C)C1=COC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(2,4-Dimethyl-5-oxazolyl)-1-(3-furyl)-1-methoxyethane (790 mg) in dry diethylether was treated with 1M anhydrous hydrogen chloride in diethylether (1.2 equivalents). The title compound was obtained as a white solid which was filtered off, washed and dried. M.p. 128.5°-130° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:C(C)(=O)C1=C(N=CO1)C;m1_m3_m2_m4:[Li]C=1OC=CC1, Reagents are:m1_m3_m2_m4:C(C)OCC;m1_m3_m2_m4:C(C)OCC, and Products are 0:O1C(=CC=C1)C(C)(O)C1=C(N=CO1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-Acetyl-4-methyloxazole (4 g) in dry diethylether was added dropwise to a stirred solution of 2-lithiofuran (1 equivalent) in diethylether at -20° C. The mixture was allowed to warm to room temperature and was then left overnight. Work-up and flash chromatography then gave the title compound as a white solid, m.p. 73°-75° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:C(C)(=O)C1=C(N=C(S1)C)C;m1_m4_m2_m5:[Li]C=1C=NC=CC1;m3:C(O)([O-])=O.[Na+], Reagents are:m1_m4_m2_m5:C(C)OCC;m1_m4_m2_m5:C(C)OCC, and Products are 0:CC=1SC(=C(N1)C)C(C)(O)C=1C=NC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-Acetyl-2,4-dimethylthiazole (2.5 g) in dry diethylether (10 ml) was added dropwise to a stirred solution of 3-lithiopyridine (from 3.5 g 3-bromopyridine) in diethylether at -70° C. After 3 hours the mixture was allowed to warm to room temperature. After a further 1 hour, aqueous sodium hydrogen carbonate was added and the organic layer was separated. The aqueous layer was extracted with diethylether. The material obtained from the combined organic layers was purified by flash chromatography to give the title compound, m.p. 107.5°-109° C. |
Here is a chemical reaction formula: Reactants are:m2:BrC1=CSC=C1;m1:C(C)(=O)C=1C(=NOC1C)C, Reagents are:, and Products are 0:CC1=NOC(=C1C(C)(O)C1=CSC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared following the general method of Example 4 but starting with 4-acetyl-3,5-dimethylisoxazole and 3-bromothiophene. |
Here is a chemical reaction formula: Reactants are:m3_m5:C(C)(=O)C=1SC=CC1;m1_m2_m4:C(CCC)[Li];m1_m2_m4:CC=1N=CSC1C, Reagents are:m3_m5:C(C)OCC;m1_m2_m4:C(C)OCC, and Products are 0:CC=1N=C(SC1C)C(C)(O)C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Butyllithium (2.5M solution in hexanes, 9.7 ml) was added dropwise to a stirred solution of 4,5-dimethylthiazole (2.5 g) in dry diethyl ether (30 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylthiophene (3.1 g) in diethyl ether (20 ml) was added dropwise. After a further 1 hour the mixture was allowed to warm to room temperature and was then worked up in the normal fashion to yield the title compound. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:CC=1N=CSC1;m0_m1_m2:ClCCCC(=O)C=1SC=CC1, Reagents are:, and Products are 0:CC=1N=C(SC1)C1(OCCC1)C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 4-methylthiazole and 4-chloro-1-(2-thienyl)-1-butanone, using the general method of Example 36. M.p. 59°-60° C., 13C Nmr (CDCl3) 17.4, 26.2, 41.2, 69.3, 86.2, 113.9, 124.2, 124.7, 126.8, 148.9, 153.1 and 175.6 ppm. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(CCC)[Li];m1_m2_m4:CC=1N=C(SC1)[Si](C)(C)C;m3_m5:C(C)(=O)C=1OC2=C(C1)C=CC=C2, Reagents are:m1_m2_m4:C(C)OCC;m3_m5:C(C)OCC, and Products are 0:O1C(=CC2=C1C=CC=C2)C(C)(O)C2=C(N=CS2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Butyllithium (2.5M solution in hexane, 1 equivalent) was added dropwise to a solution of 4-methyl-2-trimethylsilylthiazole (1 equivalent) in dry diethyl ether at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 2-acetylbenzofuran (1 equivalent) in diethyl ether was added. After 1 hour the mixture was allowed to warm to room temperature and was then quenched by the addition of saturated aqueous sodium hydrogen carbonate. Work up in the normal fashion and column chromatography on silica gel then afforded the title compound. |
Here is a chemical reaction formula: Reactants are:m3_m5:C(C)(=O)C1=CSC=C1;m1_m2_m4:C(CCC)[Li];m1_m2_m4:OCCC1=C(N=CS1)C, Reagents are:m3_m5:O1CCCC1;m1_m2_m4:O1CCCC1, and Products are 0:OCCC1=C(N=C(S1)C(C)(O)C1=CSC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: n-Butyllithium (2.5M solution in hexanes, 75 mmoles) was added to a stirred solution of 5-(2-hydroxyethyl)-4-methylthiazole (35 mmoles) in dry tetrahydrofuran (80 ml) at -70° C. under an atmosphere of dry nitrogen. After 30 minutes, 3-acetylthiophene (38 mmoles) in dry tetrahydrofuran (10 ml) was added dropwise. After 1 hour the mixture was allowed to warm to room temperature and was then stirred overnight. The normal work-up followed by column chromatography then gave the title compound. |
Here is a chemical reaction formula: Reactants are:m2:BrC=1C(=COC1)[Li];m1:C(C)(=O)C1=C(N=C(O1)C)C, Reagents are:, and Products are 0:BrC=1C(=COC1)C(C)(O)C1=C(N=C(O1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the general method of Example la but using 5-acetyl-2,4-dimethyloxazole and 4-bromo-3-lithiofuran (Liebigs Ann. Chem., 1986, 625-637), the title compound was prepared. |
Here is a chemical reaction formula: Reactants are:m2:COCC1=C(N=CS1)C;m1:C(C)(=O)C1=CSC=C1, Reagents are:, and Products are 0:COCC1=C(N=C(S1)C(C)(O)C1=CSC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared by following the general method of Example 36 but using 3-acetylthiophene and 5-methoxymethyl-4-methylthiazole. |
Here is a chemical reaction formula: Reactants are:m1:O1C=C(C=C1)C(C)(O)C1=C(N=CO1)C;m4:O;m3:B(F)(F)F;m2:C[Si](C)(C)N=[N+]=[N-], Reagents are:m5:C1=CC=CC=C1, and Products are 0:N(=[N+]=[N-])C(C)(C1=C(N=CO1)C)C1=COC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(3-Furyl)-1-(4-methyl-5-oxazolyl)ethanol (1 g) was suspended in benzene (4 ml). Trimethylsilylazide (822 μl) was added followed by boron trifluoride diethyletherate (770 μl). The mixture was stirred overnight at room temperature, then poured into water and extracted to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1:N(=[N+]=[N-])C(C)(C1=C(N=CO1)C)C1=COC=C1, Reagents are:m2:C(C)O;m3:[Pd], and Products are 0:O1C=C(C=C1)C(C)(C1=C(N=CO1)C)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The product from Example 65 in ethanol was hydrogenated in the presence of 10% palladium-on-charcoal to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:COC1=CC=C(C=C1)CCN;m1_m2_m3:ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl, Reagents are:m1_m2_m3:O1CCCC1, and Products are 0:COC1=CC=C(C=C1)CCN=C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.53 g (30 mol) of 4-methoxy-β-phenylethylamine are added dropwise to a solution of 2.96 g (10.0 mol) of triphosgene in 30 ml of dry tetrahydrofuran and the mixture is heated at the boiling point for 2 hours. The solution is cooled to room temperature and filtered and the filtrate is concentrated in vacuo. The colorless oil which remains is purified by bulb tube distillation under a pressure of 2 mmHg at a bath temperature of 220° C. to give 1.1 g of 4-methoxy-β-phenylethyl isocyanate. 0.7 g (4.0 mmol) of 4-methoxy-β-phenylethyl isocyanate and 0.4 g (3.5 mmol) of 3-ethyl-4-methyl-2-oxo-3-pyrroline are stirred with one another and the mixture is heated at 150° C. for one hour. The cooled reaction mixture is dissolved in a minimum of ethyl acetate and purified by column chromatography over silica gel 60 with the aid of the mobile phase ethyl acetate (Rf =0.5). After the eluent has been evaporated off under reduced pressure, 0.25 g of methoxy-4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolinyl-1-carboxamido)-ethyl]-benzene is obtained, and is introduced in portions into chlorosulfonic acid cooled to 0° C. After being stirred at 0° C. for one hour, this reaction mixture is poured onto ice. The sulfonic acid chloride which has precipitated is taken up in ethyl acetate. The organic phase is dried with sodium sulfate and concentrated in vacuo to give the sulfonic acid chloride as a crude product, which is dissolved in acetone and converted into 2-methoxy-5-[2-(3-ethyl-4-methyl-2-oxo-3-pyrrolinyl-1-carboxamido)-ethyl]-benzenesulfonamide with aqueous ammonia solution. The sulfonamide has a melting point of 204°-205° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C[Si](C)(C)OCCNCCO[Si](C)(C)C;m1_m2_m4_m3:C(C)N(CC)CC;m1_m2_m4_m3:C1(=CC=CC=C1)S(=O)(=O)Cl, Reagents are:m1_m2_m4_m3:C1=CC=CC=C1, and Products are 0:C[Si](OCCN(S(=O)(=O)C1=CC=CC=C1)CCO[Si](C)(C)C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 4.97 g of bis(2-trimethylsilyloxylethyl)amine, 3.03 g of triethylamine and 50 ml of benzene, 3.21 g of benzenesulfonyl chloride was added at 0° C. under stirring. After the addition, the mixture was taken out of the cooling bath and stirred further for 2 hours. The reaction mixture was filtered, mixture was taken out of the cooling bath and stirred further for 2 hours. The reaction mixture was filtered, and the filtrate was subjected to vacuum distillation. The residue was passed through a silica gel column with the eluent varying from benzene to benzen-acetic acid (9:1). As a result, 6.23 g of the title compound was obtained as a colorless oily substance. NMRδ: 7.83 (2H,d,J=8.0 Hz),7.52 (3H,m), 3.72, 3.31 (each 4H,t,J=6.5 Hz), 0.09 (18H,s) |
Here is a chemical reaction formula: Reactants are:m1:[Si](C)(C)(C(C)(C)C)OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)CCO[Si](C)(C)C(C)(C)C;m2_m4_m3:C(C)O;m2_m4_m3:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m2_m4_m3:ClCCl, and Products are 0:OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO)CCO)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 13.59 g of the tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine preparation prepared in Example 5 was dissolved in a mixed solvent containing 13.6 ml of ethanol and 27 ml of dichloromethane, and 0.272 g of p-toluenesulfonic acid monohydrate was added thereto. The mixture was refluxed under heating at 50° C. for 6 hours, and then cooled to room temperature. The crystals were collected by filtration, washed with 29.5 ml of dichloromethane and dried. As a result, 5.54 g of the title compound was obtained as crystals with a melting point of 110°-113° C. |
Here is a chemical reaction formula: Reactants are:m1:[Si](C)(C)(C(C)(C)C)OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)C1=C(C=C(C=C1)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)S(N(CCO[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C)(=O)=O)CCO[Si](C)(C)C(C)(C)C;m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, Reagents are:m3:O1CCCC1;m4:O1CCCC1, and Products are 0:OCCN(S(=O)(=O)C1=C(C=CC(=C1)S(N(CCO)CCO)(=O)=O)[Bi](C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)C1=C(C=C(C=C1)S(N(CCO)CCO)(=O)=O)S(N(CCO)CCO)(=O)=O)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.38 g of the tris(2,4-bis(N,N-bis(2-t-butyldimethylsilyloxyethyl)sulfamoyl)phenyl)bismuthine preparation obtained in Example 5 in 15 ml of tetrahydrofuran was cooled to -30° C., and 5.88 ml of a 1 M/1 tetrahydrofuran solution of tetra-n-butylammonium fluoride was gradually added droprise under stirring. After removal of the cooling bath, it was stirred further for 2 hours. Water and n-hexane were added to the reaction solution, and after vigorous shaking, the aqueous layer was separated out. The aqueous layer was washed with chloroform three times, and lyophilized. As a result, 0.67 g of the title compound as obtained. NMR (D2O)δ: 8.49 (3H,s), 7.38, 6.82 (each 3H,A Bq), 3.65 (24H,m), 3.44 (12H,t), 3.29(12H,t) |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CC(=O)C)(=O)OCC;m1_m2:C(C)NCC, Reagents are:, and Products are 0:C(C)N(C(CC(C)=O)=O)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 40 g (0.31 mol) of ethyl acetoacetate and 24 g (0.33 mol) of diethylamine were stirred in a Parr apparatus at 150° C. for 10'. The crude mixture was distilled at 115°-120° C./9 mmHg, to give 32 g of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:C(C)N(C(CC(C)=O)=O)CC;m1_m2_m3_m5:CC(=O)O[Na];m1_m2_m3_m5:O;m4:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m3_m5:C(C)O, and Products are 0:C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15.7 g (0.1 mol) of N,N-diethyl-3-oxobutyramide were mixed with 12 g (0.14 mol) of CH3COONa, 20 ml of water and 75 ml of ethanol. The solution obtained was cooled to 10° C. and 0.1 mol of freshly prepared solution of phenyldiazonium chloride [Organic Reactions, R. Adams Ed; Wiley, New York, 10, 32-33, (1951-1959)] were added dropwise. The precipitated solid was filtered, dried in vacuo yielding 22.6 g of the title compound. M.p.=63°-65° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CC(=O)C)(=O)OCC;m1_m2:C(CC)NCCC, Reagents are:, and Products are 0:C(CC)N(C(CC(C)=O)=O)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 43.4 g (43.3 mol) of ethyl acetoacetate and 33.7 g (43.3 mol) of dipropylamine were treated as described in preparation 1. The crude oil was distilled at 86°-89° C./ 0.8 mmHg, to give 44.3 g of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5_m4:C(CC)N(C(CC(C)=O)=O)CCC;m1_m2_m3_m5_m4:CC(=O)O[Na];m1_m2_m3_m5_m4:O;m1_m2_m3_m5_m4:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m3_m5_m4:C(C)O, and Products are 0:C(CC)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 18.5 g (0.1 mol) of N,N-dipropyl-3-oxobutyramide, 12 g (0.146 mol) of CH3COONa, 20 ml of water, 75 ml of ethanol and a solution of 0.1 mol of phenyldiazonium chloride were treated as described in preparation 2. The precipitated solid was filtered and dried in vacuo yielding 4.2 g of the title compound. M.p.=79°-80° C. |
Here is a chemical reaction formula: Reactants are:m2:C1(=CC=C(C=C1)S(=O)(=O)O)C;m1_m3:C(CC(=O)C)(=O)OCC;m1_m3:C(C(C)C)O, Reagents are:, and Products are 0:C(CC(=O)C)(=O)OCC(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 30 ml of ethyl acetoacetate were dissolved in 350 ml of i-butyl alcohol and a catalytic amount of p-toluensulphonic acid (PTSA) was added. The solution was refluxed for 18 h. The reaction mixture was evaporated in vacuo and the residue was dissolved in ether. The resulted solution was treated with s.s. NaHCO3. The organic layer was separated, dried over Na2SO4 and evaporated in vacuo. The crude oil was distilled at 66°-68° C./4 mmHg, to give 18.8 g of the title compound. |