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

HRID 979672
Notes
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Reaction equation

HRID 979672 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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 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 and ethyl acetate layer
  3. washis washed with water
  4. customdried
  5. customEvaporation of ethyl acetate

Sources & evidence

ORD record
ord-a8f1d3d0b4674e15bd04d7828e1f1b3c
Source dataset
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04668783

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes