Thionyl Chloride → 2-Benzyloxy-4-benzyloxycarbonylaminomethylbenzoyl chloride

HRID 619245ノート

反応式

HRID 619245 の反応式
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]1[CH:21]=[C:20]([CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:19]=[CH:18][C:14]=1[C:15](O)=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O.ClCCl>[CH2:5]([O:12][C:13]1[CH:21]=[C:20]([CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:19]=[CH:18][C:14]=1[C:15]([Cl:3])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 2

HCID 24386Thionyl ChlorideHCID 221205252-Benzyloxy-4-benzyloxycarbonylaminomethylbenzoic acid

生成物 1

HCID 221204722-Benzyloxy-4-benzyloxycarbonylaminomethylbenzoyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

Thionyl chloride (1.55 ml) and dimethylformamide (2 drops) were added to a solution of 2-benzyloxy-4-benzyloxycarbonylaminomethylbenzoic acid (7.1 g) in dichloromethane (50 ml), and the mixture was refluxed under heating for 1.5 hours. After the reaction, the solvent was evaporated under reduced pressure to give 2-benzyloxy-4-benzyloxycarbonylaminomethylbenzoyl chloride as crystals. Then, the crystals were dissolved in acetonitrile (50 ml), and the solution was dropwise added to a solution of 4-aminopyridine (1.42 g) and diisopropylethylamine (5.27 ml) in acetonitrile (50 ml) under ice-cooling. The mixture was stirred at room temperature for 4 hours. After the reaction, water was added, and the mixture was extracted with chloroform. The extract was washed with water and dried. The solvent was evaporated under reduced pressure and the obtained crystals were recrystallized from ethyl acetate-hexane to give N-(4-pyridyl)-2-benzyloxy-4-benzyloxycarbonylaminomethylbenzamide as crystals.

後処理

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1.5 hours
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-96dd05f2c28444c3971ebcb2dce71061
出典データセット
uspto-grants-1999_09
特許番号
US05958944

反応ノート

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