4-Chlorobutyryl chloride → [4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

HRID 48015ノート

反応式

HRID 48015 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10].[CH3:12][O:13][N:14]([CH3:24])[C:15](=[O:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:5][CH2:6][CH2:7][CH2:8][C:9]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][C:15]([N:14]([O:13][CH3:12])[CH3:24])=[O:23])=[CH:22][CH:21]=1)=[O:10]

参加物

5

反応物 3

HCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10419762N-Methoxy-N-methyl-2-phenylacetamide

生成物 1

HCID 9857023[4-(4-Chloro-1-oxobutyl)]-N-methoxy-N-methyl benzeneacetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Cool a slurry of aluminum chloride (87 g, 650 mmol) in methylene chloride (100 mL) with an ice bath. Add 4-chlorobutyryl chloride (51 g, 360 mL) dropwise over 0.5 hours. Add N-methoxy-N-methyl-benzeneacetamide (53 g; 300 mmol) over 0.5 hours. Allow the resultant solution to warm to room temperature. Then heat at reflux for 6 hours. Cool the solution to room temperature. Pour the solution into ice (1 L) and add methylene chloride (1 L). Separate the organic phase. Extract the aqueous phase with methylene chloride (2×500 mL). Dry the combined organics over anhydrous magnesium sulfate and concentrate to provide a solid which contains a ca. 1:1 mixture of the title compound and the meta isomer.

後処理

  1. temperatureThen heat
  2. temperatureat reflux for 6 hours
  3. customSeparate the organic phase
  4. extractionExtract the aqueous phase with methylene chloride (2×500 mL)
  5. dry with materialDry the combined organics over anhydrous magnesium sulfate
  6. concentrationconcentrate
  7. customto provide a solid which

出典と根拠

ORDレコード
ord-746321b5ab7a4de6bedeafbd7779cd02
出典データセット
uspto-grants-2004_03
特許番号
US06700012B2

反応ノート

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