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

HRID 1975371Notes

Reaction equation

HRID 1975371 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-a6750e20951e462abb13357364492fbf
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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