Chloroacetic Acid → 2-Chloro-N-methyl-N-phenylacetamide

HRID 1657520Notes

Reaction equation

HRID 1657520 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:14][CH2:15][C:16](O)=[O:17]>O>[CH3:6][N:7]([C:16](=[O:17])[CH2:15][Cl:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 7515N-Methylaniline2×HCID 24813Phosphorus oxychloride2×

Product 1

HCID 757972-Chloro-N-methyl-N-phenylacetamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

76.75g (0.50 moles) of phosphoryl chloride and 107g (1.00 moles) of N-methyl aniline were added to 99.2g (1.05 moles) of monochloracetic acid. Alternate additions of 10% of the total amount of each of the N-methyl aniline and of the phosphoryl chloride were made with stirring at a temperature of 60° to 70°C over a period of 75 minutes. The reaction mixture was then stirred at 100° to 110°C for 4 hours, after which the reaction mixture was cooled to 70° to 80°C and then poured into warm water. The aqueous suspension was stirred vigorously whilst cooling until the product crystallised and then cooled further until the temperature reached 30° to 35°C. The precipitated crystalline product was separated from the aqueous phase by filtration and then washed with water. The washed product was dried in an oven at a temperature of 50° to 60°C. 157g of dry off-white crystals of N-methyl chloro acetanilide having a melting point of 69°C were obtained. The yield was 85.5% based on the theoretical yield from the N-methyl aniline in the starting material.

Workup

  1. stirringThe reaction mixture was then stirred at 100° to 110°C for 4 hours
  2. temperatureafter which the reaction mixture was cooled to 70° to 80°C
  3. additionpoured
  4. stirringThe aqueous suspension was stirred vigorously
  5. temperaturewhilst cooling until the product
  6. customcrystallised
  7. temperaturecooled further until the temperature
  8. customreached 30° to 35°C
  9. customThe precipitated crystalline product was separated from the aqueous phase by filtration
  10. washwashed with water
  11. customThe washed product was dried in an oven at a temperature of 50° to 60°C

Sources & evidence

ORD record
ord-388843e6eb494eef8c3c99d71ebfbb96
Source dataset
uspto-grants-1976_06
Patent number
US03960948

Reaction notes

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