5-Chlorovaleryl chloride → 1-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one

HRID 963339

反応式

HRID 963339 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([O:11]C)[CH:8]=[CH:7][C:6]=1[Cl:13])(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)CCl>[C:1]([NH:4][C:5]1[C:6]([Cl:13])=[CH:7][C:8]([C:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][Cl:18])=[C:9]([OH:11])[CH:10]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 19081918N-(2-Chloro-5-methoxyphenyl)acetamide

生成物 1

HCID 190818791-(4-Acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one収率 70.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

N-Acetyl-2-chloro-5-methoxyaniline (10.0 g, 50 mmol), aluminum chloride (13.3 g, 100 mmol), and 5-chloropentanoyl chloride (11.7 g, 75 mmol) were combined in ethylene dichloride (100 mL) and the mixture was stirred at room temperature and under nitrogen for 7 days. The mixture was then poured onto crushed ice and extracted into methylene chloride. The methylene chloride extract was washed with water and then dried. The solvent was evaporated in vacuo. Crystallization of the residue from ethyl acetate/hexane gave 1-(4-acetylamino-5-chloro-2-hydroxyphenyl)-5-chloropentan-1-one (10.18 g, 35.1 mmol), m.p. 126°-128° C.

後処理

  1. additionThe mixture was then poured
  2. customonto crushed ice
  3. extractionextracted into methylene chloride
  4. extractionThe methylene chloride extract
  5. washwas washed with water
  6. customdried
  7. customThe solvent was evaporated in vacuo
  8. customCrystallization of the residue from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-1949f987f8d045ae9e573ed8d6558f1a
出典データセット
uspto-grants-1998_06
特許番号
US05763458

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