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

HRID 223614
Notes
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Reaction equation

HRID 223614 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 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-c13df734c2bc4353a09b8b9cf85c4fd0
Source dataset
uspto-grants-1982_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04355160

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes