邻氯苯基硫脲

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Chloroaniline (23, 10.52 mL, 100 mmol) was dissolved in conc. HCl (9 mL) followed by H2O (25 mL). The mixture was heated at reflux for 30 minutes then allowed to cool to rom temperature. To this solution was added NH4SCN (7.61 g, 100 mmol) and the mixture was heated at reflux overnight. The reaction was allowed to cool to room temperature and a solid formed. The water layer was decanted off and the solid was dissolved in CH2Cl2 and the organic layer was washed in brine. The organic layer was dried over MgSO4, filtered and evaporated to give a residue, which was purified by flash silica gel chromatography. The mixture was heated at reflux for 30 minutes to cool the mixture was heated at reflux overnight a solid formed The water layer was decanted off the solid was dissolved in CH2Cl2 the organic layer was washed in brine The organic layer was dried over MgSO4 filtered evaporated to give a residue, which was purified by flash silica gel chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2-Chloroaniline (23, 10.52 mL, 100 mmol) was dissolved in conc. HCl (9 mL) followed by H2O (25 mL). The mixture was heated at reflux for 30 minutes then allowed to cool to rom temperature. To this solution was added NH4SCN (7.61 g, 100 mmol) and the mixture was heated at reflux overnight. The reaction was allowed to cool to room temperature and a solid formed. The water layer was decanted off and the solid was dissolved in CH2Cl2 and the organic layer was washed in brine. The organic layer was dried over MgSO4, filtered and evaporated to give a residue, which was purified by flash silica gel chromatography. The mixture was heated at reflux for 30 minutes to cool the mixture was heated at reflux overnight a solid formed The water layer was decanted off the solid was dissolved in CH2Cl2 the organic layer was washed in brine The organic layer was dried over MgSO4 filtered evaporated to give a residue, which was purified by flash silica gel chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (50 mg) was allowed to react with 2-chlorophenyl thiourea (26.7 mg) as described in Example 154, step (a), to give 58 mg (75%) of methyl 4-{2-[(2-chlorophenyl)amino]-(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.66 (s, 3H), 3.82 (s, 3H), 7.04 (m, 1H), 7.32-7.38 (m, 2H), 7.47 (dd, 1H, J=1.4, 8.7 Hz), 8.12 (s, 1H), 8.56 (dd, 1H, J=1.4, 8.3 Hz), 9.75 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C16H13ClN2O2S3, 396.94 (M+H), found 397.1.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (50 mg) was allowed to react with 2-chlorophenyl thiourea (26.7 mg) as described in Example 154, step (a), to give 58 mg (75%) of methyl 4-{2-[(2-chlorophenyl)amino]-(1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.66 (s, 3H), 3.82 (s, 3H), 7.04 (m, 1H), 7.32-7.38 (m, 2H), 7.47 (dd, 1H, J=1.4, 8.7 Hz), 8.12 (s, 1H), 8.56 (dd, 1H, J=1.4, 8.3 Hz), 9.75 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C16H13ClN2O2S3, 396.94 (M+H), found 397.1.

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 74 mg (1.2 mmol) of (2-chlorophenyl)-thiourea is added to a suspension of 124 mg (0.33 mmol) of 8-(2-bromo-acetyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 3.5 mL of ethanol. The mixture is stirred at 90° C. for 6 hours then the mixture is cooled to room temperature. The solvent is evaporated, then the product is purified by preparative LCMS. After drying, 41 mg (27%) of 8-[2-(2-chlorophenylamino)-thiazol-4-yl]-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a beige solid. the mixture is cooled to room temperature The solvent is evaporated the product is purified by preparative LCMS After drying

反应条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 210 Parts of sulfuryl chloride were added within about 2 hours at a temperature of 35°-40° C. to a stirred mixture of 186.5 parts of 2-chlorophenylthiourea, 500 parts of toluene, 300 parts of chlorobenzene and 11 parts of sodium carbonate. The gas development being terminated, 250 parts of water were added, the solvent mixture was distilled off with steam, and the remaining aqueous phase was combined with 500 parts of 30% hydrochloric acid. Filtration from the undissolved matter was carried out at about 90° C., the filtrate was cooled to about 20° C., and the free amine was precipitated from the 2-amino-4-chlorobenzothiazole dissolved as hydrochloride by adding excess sodium hydroxide solution until a final pH of 8.5-9.0 was adjusted. The product was suction-filtered, washed to neutral with water, and dried. 170 Parts of 2-amino-4-chlorobenzothiazole having a melting point of 199°-200° C. (92.4% of th.) were obtained. The gas development being terminated 250 parts of water were added the solvent mixture was distilled off with steam Filtration from the undissolved matter was carried out at about 90° C. the free amine was precipitated from the 2-amino-4-chlorobenzothiazole dissolved as hydrochloride by adding excess sodium hydroxide solution until a final pH of 8.5-9.0 The product was suction-filtered washed to neutral with water dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Synthesis was performed from N-(2-chlorophenyl)thiourea and 2-bromo-butyric acid according to Method C1. Synthesis