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

HRID 48015노트

반응식

HRID 48015 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-746321b5ab7a4de6bedeafbd7779cd02
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06700012B2

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