Water → alpha-Hydroxy[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

HRID 1165938Notes

Reaction equation

HRID 1165938 reaction equation
[Cl:1][C:2]([Cl:16])([Cl:15])[CH2:3][O:4][C:5]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH:13]=[O:14])[N:12]=1)=[O:6].OP([O-])(O)=O.[K+].O.[C-:24]#[N:25].[K+]>CN(C)C=O>[OH:14][CH:13]([C:11]1[N:12]=[C:8]([NH:7][C:5]([O:4][CH2:3][C:2]([Cl:1])([Cl:15])[Cl:16])=[O:6])[S:9][CH:10]=1)[C:24]#[N:25]

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 516951Monobasic potassium phosphateHCID 127632072-(beta,beta,beta-Trichloroethoxycarbonyl)amino-4-formylthiazole

Product 1

HCID 15137534alpha-Hydroxy[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.0 g. of 2-(β,β,β-trichloroethoxycarbonyl)amino-4-formylthiazole, 0.87 g. of KH2PO4, 6 ml. of water and 4 ml. of dimethylformamide is added 0.33 g. of KCN at room temperature and the mixture is stirred for 30 minutes. The reaction mixture is extracted with ethyl acetate and the ethyl acetate layer is washed with water and dried. Evaporation of ethyl acetate gives α-hydroxy-[2-(β,β,β-trichloroethoxycarbonyl)aminothiazol-4-yl]-acetonitrile 1.127 g.

Workup

  1. additionTo a mixture of 1.0 g
  2. extractionThe reaction mixture is extracted with ethyl acetate
  3. washthe ethyl acetate layer is washed with water
  4. customdried
  5. customEvaporation of ethyl acetate

Sources & evidence

ORD record
ord-69c189de4db5462287b783aa9d24e450
Source dataset
uspto-grants-1990_03
Patent number
US04912212

Reaction notes

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