Chloroacetyl chloride → Methyl 2-((2-chloroacetyl)methylamino)benzoate

HRID 1381185Notes

Reaction equation

HRID 1381185 reaction equation
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[Cl:19][CH2:20][C:21](Cl)=[O:22]>CC(C)=O.O>[CH3:1][N:2]([C:21](=[O:22])[CH2:20][Cl:19])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6826Methyl N-methylanthranilateHCID 11430Potassium Carbonate

Product 1

HCID 21813533Methyl 2-((2-chloroacetyl)methylamino)benzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

25 Grams of methyl o-methylaminobenzoate was dissolved in 125 ml of acetone, to this solution was added a solution prepared by dissolving 20.92 g of potassium carbonate in 60 ml of water. Under an ice-cooled condition, 17.95 g of chloroacetyl chloride was added dropwise thereto, then the reaction mixture was stired at a room temperature for 1 hour. Acetone was removed by distillation, the residue obtained was extracted with chloroform, then the chloroform layer was washed with water, dried and the solvent was removed by distillation. The residue thus obtained was purified by a silica gel column chromatography to obtain 16.80 g of N-methyl-o-methoxycarbonyl-α-chloroacetanilide in the form of colorless oily substance.

Workup

  1. additionwas added a solution
  2. customprepared
  3. additionwas added dropwise
  4. customAcetone was removed by distillation
  5. customthe residue obtained
  6. extractionwas extracted with chloroform
  7. washthe chloroform layer was washed with water
  8. customdried
  9. customthe solvent was removed by distillation
  10. customThe residue thus obtained
  11. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-b473d2a277c1486b8662bd7f857e6e1c
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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