1-Bromo-3-chloropropane → 1-[3-Acetylamino-4-(3-chloropropoxy)phenyl]ethanone

HRID 264172노트

반응식

HRID 264172 반응식
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])(=[O:3])[CH3:2].[Cl:15][CH2:16][CH2:17][CH2:18]Br>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[O:11][CH2:18][CH2:17][CH2:16][Cl:15])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 80061-Bromo-3-chloropropaneHCID 283886n-(5-Acetyl-2-hydroxyphenyl)acetamide

생성물 1

HCID 100159331-[3-Acetylamino-4-(3-chloropropoxy)phenyl]ethanone수율 78.8%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl]ethanone (7.7 g, 40 mmol), K2CO2 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the filtrate yielded 8.5 g of a white solid. The solid was recrystallized from toluene and then from ethanol to afford 6.5 g of an off-white solid. A 3.3 g sample of this material was flash chromatographed on silica gel with ethyl acetate as eluent. Concentration of the appropriate fractions afforded 2.8 g of a solid. The solid was recrystallized from toluene and then from ethanol-water to yield 2.2 g (51%) of a solid, m.p.=124°-126° C.

후처리

  1. temperaturewas refluxed for 16 hours
  2. filtrationfiltered

출처 및 근거

ORD 기록
ord-2171d0b095f24fdcbe85c2efe7a9701a
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646161

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