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

HRID 266967ノート

反応式

HRID 266967 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-9a32fce240f74d7385f4086b098da935
出典データセット
uspto-grants-1997_07
特許番号
US05652241

反応ノート

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