Methyl 2-amino-4-chloro-5-nitrobenzoate → 4-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitro-benzoic acid methyl ester

HRID 1858062ノート

反応式

HRID 1858062 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH2:14].[CH3:16][C:17]1[CH:18]=[C:19]([CH2:24][C:25](Cl)=[O:26])[CH:20]=[C:21]([CH3:23])[CH:22]=1>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Cl:13])=[CH:6][C:5]=1[NH:14][C:25](=[O:26])[CH2:24][C:19]1[CH:18]=[C:17]([CH3:16])[CH:22]=[C:21]([CH3:23])[CH:20]=1

参加物

3

反応物 2

HCID 15895692Methyl 2-amino-4-chloro-5-nitrobenzoateHCID 15895699(3,5-Dimethylphenyl)acetyl chloride2 回

生成物 1

HCID 543134564-Chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-nitro-benzoic acid methyl ester収率 72.4%

実験手順

To a suspension of 2-amino-4-chloro-5-nitrobenzoic acid methyl ester (989 mg in 15 mL of dry 1,2-dichloroethane) was added a solution of (3,5-dimethylphenyl)acetyl chloride (860 mg in 5 mL dry 1,2-dichloroethane) and the mixture heated at reflux on an oil bath. After 18 hours, an additional portion of (3,5-dimethylphenyl)acetyl chloride (274 mg in 1.5 mL dry 1,2-dichloroethane) was added and the mixture heated at reflux for an additional 5 hours. At this time the reaction was cooled and the solvent removed in vacuo. Recrystallization of the crude product from methanol gave the title compound (1.17 g).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux on an oil bath
  3. temperaturethe mixture heated
  4. temperatureat reflux for an additional 5 hours
  5. temperatureAt this time the reaction was cooled
  6. customthe solvent removed in vacuo
  7. customRecrystallization of the crude product from methanol

出典と根拠

ORDレコード
ord-0a55e9c5fc4046499b7ad5b86da0edc5
出典データセット
uspto-grants-2000_11
特許番号
US06150352

反応ノート

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