Chloroacetyl chloride → 2-chloro-N-(2,4-dimethoxyphenyl)acetamide

HRID 81825

반응식

HRID 81825 반응식
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:19][CH2:20][C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=1[O:2][CH3:1])=[O:22]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 176522,4-Dimethoxyaniline

생성물 1

HCID 3038242-chloro-N-(2,4-dimethoxyphenyl)acetamide수율 99.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2,4-dimethoxy aniline (30.6 g, 0.2 mol), triethylamine (27.9 mL, 0.2 mol) in 600 mL methylene chloride was stirred at 0° C. under nitrogen. Chloroacetyl chloride (16 mL, 0.2 mol) was added dropwise, and the reaction mixture was stirred for 15 minutes at 0° C., and then stirred for an additional two hours during which time the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 1N HCl, followed by saturated aqueous sodium bicarbonate. The aqueous mixture was partitioned with EtOAc, and the organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 45.58 g of crude 2-Chloro-N-(2,4-dimethoxy-phenyl)-acetamide. MS (M+H)=230.

후처리

  1. stirringthe reaction mixture was stirred for 15 minutes at 0° C.
  2. stirringstirred for an additional two hours during which time the reaction mixture
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched by addition of 1N HCl
  5. customThe aqueous mixture was partitioned with EtOAc
  6. customthe organic phase was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-16494d629adc42cca543ccac2ad3a029
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846705B2

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