Thionyl Chloride → 4-Methoxy-2-nitrobenzoyl chloride

HRID 2036550

반응식

HRID 2036550 반응식
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.S(Cl)([Cl:17])=O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:17])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 2886574-Methoxy-2-nitrobenzoic acid

생성물 1

HCID 214740534-Methoxy-2-nitrobenzoyl chloride

반응 조건

온도
75 °C

실험 절차

A mixture of 4-methoxy-2-nitrobenzoic acid 1 (1.0 g) and thionyl chloride (5 mL) was heated at 75° C. for overnight under nitrogen atmosphere. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated at 40° C. under vacuum to give 4-methoxy-2-nitrobenzoyl chloride as a yellow solid which was used in the next step without further purification. To a solution of 4-methoxy-2-nitrobenzoyl chloride (1.0 g) in 10 mL THF was added ammonium hydroxide (5 mL) drop-wise (exothermic). The resulting mixture was stirred at room temperature for 30 min. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was evaporated to give 4-methoxy-2-nitrobenzamide 2 which was purified by triturating with methyl tert-butyl ether. Pink solid (1.05 g, 100%). 1H NMR (400 MHz, CDCl3): δ 3.89 (s, 3H); 5.87 (br s, 2H); 7.13-7.15 (m, 1H); 7.25-7.26 (m, 1H); 7.47-7.52 (m, 1H).

후처리

  1. customThe reaction mixture was evaporated at 40° C. under vacuum

출처 및 근거

ORD 기록
ord-c80969dfd38e4a5d91c32a620bd4c802
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575185B2

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