Chloroacetyl chloride → N-Methyl-4-(2-chloroacetamido)benzoic acid

HRID 1975371ノート

反応式

HRID 1975371 の反応式
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH2:22][C:23]([N:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[CH3:1])=[O:24]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 663454-(Methylamino)benzoic acidHCID 81531Diisopropylethylamine

生成物 1

HCID 7010325N-Methyl-4-(2-chloroacetamido)benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

The starting material is prepared as follows: There are added to 30 g of 4-(N-methylamino)benzoic acid in 500 ml of dichloromethane 30.7 g of Hunig base and, at 5°, 24.6 g of chloroacetyl chloride in 50 ml of dichloromethane. After stirring for 2 hours at RT, the suspension is concentrated by evaporation, and the residue is digested with water, filtered with suction and washed with 1N hydrochloric acid. The mixture is digested with ether and filtered with suction, yielding 4-(N-chloroacetyl-N-methylamino)benzoic acid having a melting point (186°) of 195°-197°. 10 g thereof are boiled under reflux for 2 hours in 150 ml methylene chloride with 5 drops of pyridine with 15 ml of thionyl chloride, concentrated by evaporation and recrystallised from hexane. The resulting 4-(N-chloroacetyl-N-methylamino)benzoic acid chloride melts at 61°-63°.

後処理

  1. customThe starting material is prepared
  2. concentrationthe suspension is concentrated by evaporation
  3. filtrationfiltered with suction
  4. washwashed with 1N hydrochloric acid
  5. filtrationfiltered with suction

出典と根拠

ORDレコード
ord-a6750e20951e462abb13357364492fbf
出典データセット
uspto-grants-1994_02
特許番号
US05286728

反応ノート

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