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

HRID 233167ノート

反応式

HRID 233167 の反応式
[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].C([O-])([O-])=O.[K+].[K+].[Cl:21][CH2:22][CH2:23][CH2:24]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][CH2:24][CH2:23][CH2:22][Cl:21])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 283886n-(5-Acetyl-2-hydroxyphenyl)acetamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl]ethanone (7.7 g, 40 mmol), K2CO3 (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.

後処理

  1. temperaturewas refluxed for 16 hours
  2. filtrationfiltered

出典と根拠

ORDレコード
ord-c21d22a7bfd44497ac0f2b5e53d4f552
出典データセット
uspto-grants-1997_01
特許番号
US05591745

反応ノート

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