Thionyl Chloride → N-(2,2,2-Trichloroethyloxycarbonyl)-glycyl chloride

HRID 1706616Notes

Reaction equation

HRID 1706616 reaction equation
[Cl:1][C:2]([Cl:13])([Cl:12])[CH2:3][O:4][C:5]([NH:7][CH2:8][C:9](O)=[O:10])=[O:6].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]([Cl:13])([Cl:12])[CH2:3][O:4][C:5]([NH:7][CH2:8][C:9]([Cl:16])=[O:10])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11139569Glycine, N-[(2,2,2-trichloroethoxy)carbonyl]-

Product 1

HCID 20357786N-(2,2,2-Trichloroethyloxycarbonyl)-glycyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 25 parts of N-[(2,2,2-trichloroethoxy)carbonyl]glycine in 250 parts by volume of toluene is added dropwise with stirring 20 parts of thionyl chloride. The resultant reaction mixture is heated on a steam bath for about 2 hours, then the solvent and excess of thionyl chloride are removed by distillation to afford {[(2,2,2-trichloroethoxy)carbonyl]amino} acetyl chloride represented by the following formula

Workup

  1. customThe resultant reaction mixture
  2. temperatureis heated on a steam bath for about 2 hours
  3. customthe solvent and excess of thionyl chloride are removed by distillation

Sources & evidence

ORD record
ord-617219c8a8a74795b30ed9f6c66afc78
Source dataset
uspto-grants-1980_06
Patent number
US04208327

Reaction notes

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