2-chloro-N-(2-methoxyethyl)acetamide → N-[2-(cyclopent-2-enyl)phenyl]-N-(2-methoxyethyl)-2-chloroacetamide

HRID 2107511

반응식

HRID 2107511 반응식
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:9])[CH2:7][Cl:8].[CH:10]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2NC(=O)CCl)[CH2:14][CH2:13][CH:12]=[CH:11]1>>[CH:10]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6](=[O:9])[CH2:7][Cl:8])[CH2:14][CH2:13][CH:12]=[CH:11]1

참가 물질

3

반응물 2

HCID 23860482-chloro-N-(2-methoxyethyl)acetamideHCID 14880661N-[2-(cyclopent-2-enyl)phenyl]-2-chloroacetamide

생성물 1

HCID 14880660N-[2-(cyclopent-2-enyl)phenyl]-N-(2-methoxyethyl)-2-chloroacetamide

실험 절차

The preparation of N-[2-(cyclopent-2-enyl)phenyl]-N-(2-methoxyethyl)-2-chloroacetamide was conducted in a fashion analogous to example 2. Reaction of 30.00 g (188.4 mmol) of 2-(cyclopent-2-enyl)aniline, 75.75 g (750 mmol}of triethylamine, and 70.91 g (750 mmol) of 2-chloroethyl methyl ether at 100° C. in a closed, 500 mL flask for 56 hr. afforded ca. 40 g of a crude product consisting of, in part, 90.05 wt % of N-(2-methoxyethyl)-2-(cyclopent-2-enyl)aniline and 7.24 wt % of 2-(cyclopent-2-enyl)aniline. Acylation of this material with 2-chloroacetyl chloride provided ca. 50 g of a product consisting of, in part, 89.35 wt % of N-[2- cyclopent-2-enyl)phenyl]-N-(2-methoxyethyl)-2-chloroacetamide and 8.84 wt % of N-[2-(cyclopent-2-enyl)phenyl]-2-chloroacetamide. This material was purified by column chromatograph then bulb-to-bulb distillation (bp 165-175°C/1 mm/Hg).

후처리

  1. customThis material was purified by column chromatograph
  2. distillationbulb-to-bulb distillation (bp 165-175°C/1 mm/Hg)

출처 및 근거

ORD 기록
ord-aca28a9dcf6a419e9e542381d2b981e1
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04935053

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