Pyridine → N-chloroacetyl-N-phenylglycine methyl ester

HRID 1940618Notes

Reaction equation

HRID 1940618 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH2:4][N:5]([C:21](=[O:22])[CH2:20][Cl:19])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 571509Methyl 2-(phenylamino)acetate

Product 1

HCID 21463537N-chloroacetyl-N-phenylglycine methyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To methylene chloride (20 ml) was added N-phenylglycine methyl ester (2.02 g, 10 mmol) and pyridine (1.58 g, 20 mmol) and the mixture was stirred. To the mixture was added dropwise a solution of chloroacetyl chloride (1.13 g, 10 mmol) in methylene chloride (3 ml) at room temperature and the resulting mixture was stirred for 15 hours, washed with water, dried and evaporated. The resultant residue was crystallized from isopropyl ether to give N-chloroacetyl-N-phenylglycine methyl ester (1.67 g, 70%) as a colorless powder.

Workup

  1. stirringthe resulting mixture was stirred for 15 hours
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customThe resultant residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-fa0f3908ea2d449ca8c20449227196e8
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

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