Chloroacetonitrile → 4-Amino-2-phenyl-1,3-thiazole-5-carbonitrile

HRID 262034Notes

Reaction equation

HRID 262034 reaction equation
[N:1]#[C:2][NH2:3].[C:4](OCC)(=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Na].Cl[CH2:17][C:18]#[N:19]>C(O)C>[C:5]1([C:4]2[S:11][C:17]([C:18]#[N:19])=[C:2]([NH2:3])[N:1]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 9864CyanamideHCID 578278Ethyl thiobenzoateHCID 5360545Sodium

Product 1

HCID 125263524-Amino-2-phenyl-1,3-thiazole-5-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

21 parts of cyanamide and 83 parts of ethyl thiobenzoate are successively introduced into a solution of 12.5 parts of sodium in 260 parts of ethanol, and the mixture is refluxed for one hour at 78° C. It is then left to stand for 12 hours, 40 parts of chloroacetonitrile are added, and the reaction mixture is refluxed for one hour at 78° C. The product is precipitated by means of 300 parts of water, and filtered off. 78 parts of 2-phenyl-4-amino-5-cyano-thiazole (78% of theory) of melting point 178°-179° C. are obtained.

Workup

  1. waitIt is then left
  2. temperaturethe reaction mixture is refluxed for one hour at 78° C
  3. customThe product is precipitated by means of 300 parts of water
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-4e8e4d7e158f4368a18f6760f5a635f1
Source dataset
uspto-grants-1979_05
Patent number
US04153607

Reaction notes

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