1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-Acetoxybenzamide

HRID 2113734

反応式

HRID 2113734 の反応式
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](O)=[O:9])(=[O:3])[CH3:2].[NH2:14]CC1SC=CC=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([NH2:14])=[O:9])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 34005(2-Thienylmethyl)amineHCID 757711-HydroxybenzotriazoleHCID 2386693-Acetoxybenzoic acid

生成物 1

HCID 2761253-Acetoxybenzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-acetoxybenzoic acid (8.1 mg, 0.0450 mmol), 5-aminomethyl-thiophene 18d (22.3 mg, 0.0473 mmol), 1-hydroxybenzotriazole (HOBt, 4.7 mg, 0.0348 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDC, 8.5 mg, 0.0443 mmol) was dissolved in DMF (0.6 ml) and stirred overnight at r.t. Work-up (AcOEt/H2O; brine/Na2SO4), concentration, filtration over a silica gel plug (EtOAc) and evaporation gave the intermediate 3-acetoxybenzamide, which was deacetylated by stirring in MeOH (2 ml) and Et3N (0.4 ml) for 1 h at 55° C. Evaporation gave 28.5 mg (103%) of the title 3-hydroxy-benzamide as a colorless oil.

後処理

  1. concentration(AcOEt/H2O; brine/Na2SO4), concentration, filtration
  2. customover a silica gel plug (EtOAc) and evaporation

出典と根拠

ORDレコード
ord-62b072ee28a2476c855b0635d24cefba
出典データセット
uspto-grants-2008_10
特許番号
US07432286B1

関連ノート

読み込み中…