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

HRID 38410

反応式

HRID 38410 の反応式
[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]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 176522,4-Dimethoxyaniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28c78f0b87814c96b80a9efd1ceacb5d
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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