Iodine → 2-Amino-4-Phenylthiazole-5-carbonitrile

HRID 604483Notes

Reaction equation

HRID 604483 reaction equation
Br[CH:2]([C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].[NH2:13][C:14]([NH2:16])=[S:15].II.[NH4+].[OH-]>O>[NH2:16][C:14]1[S:15][C:2]([C:3]#[N:4])=[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:13]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14923Ammonium HydroxideHCID 2723790ThioureaHCID 119615962-Bromo-3-oxo-3-phenylpropanenitrile

Product 1

HCID 214555522-Amino-4-Phenylthiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Bromo-3-oxo-3-phenylpropionitrile (0.5 g, 3.4 mmol) was mixed with thiourea (0.52 g, 6.8 mmol) and iodine (0.43 g, 3.4 mmol) and the mixture was heated on a steam bath for 12 h. It was then diluted with water and made alkaline with saturated aqueous NH4OH, and extracted with ethyl acetate. The organic phases were washed with water and brine, dried over sodium sulfate, and evaporated to dryness to give the crude product, which was used in the next reaction without any further purification. Yield: 0.2 g, 29%.

Workup

  1. temperaturethe mixture was heated on a steam bath for 12 h
  2. extractionextracted with ethyl acetate
  3. washThe organic phases were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-03d78c88d23b42f9abb204f8b42379f8
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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