Dimethylformamide → N-(2,2,2-Trichloroethyloxycarbonyl)-glycyl chloride

HRID 2083806Notes

Reaction equation

HRID 2083806 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].C(Cl)(=O)C([Cl:17])=O.CN(C=O)C>C(Cl)Cl>[Cl:1][C:2]([Cl:13])([Cl:12])[CH2:3][O:4][C:5]([NH:7][CH2:8][C:9]([Cl:17])=[O:10])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 11139569Glycine, N-[(2,2,2-trichloroethoxy)carbonyl]-

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2,2,2-Trichloroethyloxycarbonyl)-glycine (0.75 g, 3 mMol) is suspended in CH2Cl2 (30 ml) and the mixture is stirred under N2 with ice-bath cooling. Oxalyl chloride (0.28 ml, 3.3 mMol) and DMF (0.023 ml, 0.3 mMol) are added thereto, and the mixture is stirred for 1 hour in the cold. The resulting solution is washed with ice-cold water and ice-cold brine, dried briefly over Na2SO4, and filtered. This solution of N-(2,2,2-trichloroethyloxycarbonyl)glycyl chloride is used immediately in the next step.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred for 1 hour in the cold
  3. washThe resulting solution is washed with ice-cold water and ice-cold brine
  4. dry with materialdried briefly over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0e3d3b4092a643699822ac939fd6cd7d
Source dataset
uspto-grants-1978_04
Patent number
US04086423

Reaction notes

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