p-Toluenesulfonic acid → HCID 178498283, 화합물

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C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH2:23])[CH:16]=1.[Cl:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C([O-])(O)=O.[Na+]>>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH:23][C:28](=[NH:29])[C:27]2[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:26]=2[Cl:25])[CH:16]=1

참가 물질

반응물 4

HCID 6101p-Toluenesulfonic acid

HCID 1090002-Chloro-4-fluorobenzonitrile

HCID 516892Sodium Bicarbonate

HCID 2734814Methyl 3-Amino-4-methoxybenzoate

생성물 1

HCID 178498283HCID 178498283, 화합물수율 72%

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온도: 160 °C

실험 절차

Anhydrous p-toluene sulfonic acid (41.99 g, 220.76 mmol) was melted at 120° C. and 3-amino-4-methoxy benzoic acid methyl ester (20 g, 110.38 mmol) obtained in step 1 of Preparation Example 1 and 2-chloro-4-fluorobenzonitrile (25.76 g, 165.57 mol) were added thereto and stirred at 160° C. for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (26.70 g, 79.47 mmol) in a yield of 72%.