Chloromethyl Methyl Ether → alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

HRID 1577464

반응식

HRID 1577464 반응식
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4].Cl[CH2:17][O:18][CH3:19].[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:5]([CH2:17][O:18][CH3:19])[C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4]

참가 물질

6

반응물 3

HCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 20570575alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide

생성물 1

HCID 20554723alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide수율 90%

시약·촉매·용매 2

HCID 165294Benzyltriethylammonium bromide촉매HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a mixture containing alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide (11.0 g; 0.048 mole), 10 ml. of (chloromethyl)methyl ether and 3.0 g. of benzyltriethylammonium bromide in 100 ml. of methylene chloride was added 50 ml. of a 50% sodium hydroxide solution. The temperature of the reaction mixture increased to 40° C. The reaction mixture was stirred for 1 hour after which time the layers were separated, and the organic methylene chloride layer was concentrated in vacuo yielding a white solid. The white solid was recrystallized from isopropanol to yield alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (11.8 g; 90% yield) as a white solid having a melting point of 104°-106° C. and the following analysis:

후처리

  1. customwere separated
  2. concentrationthe organic methylene chloride layer was concentrated in vacuo
  3. customyielding a white solid
  4. customThe white solid was recrystallized from isopropanol

출처 및 근거

ORD 기록
ord-eaf4e6cbbedc4da29f6bd74118158f34
출처 데이터셋
uspto-grants-1981_09
특허 번호
US04288242

연결된 노트

불러오는 중…