Thionyl Chloride → 4-Methoxy-2-nitrobenzoyl chloride

HRID 2036550

反応式

HRID 2036550 の反応式
[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

参加物

3

反応物 2

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

生成物 1

HCID 214740534-Methoxy-2-nitrobenzoyl chloride

反応条件

温度
75 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-c80969dfd38e4a5d91c32a620bd4c802
出典データセット
uspto-grants-2013_11
特許番号
US08575185B2

関連ノート

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