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

HRID 1960003Notes

Reaction equation

HRID 1960003 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](F)[CH:7]=1)[CH2:3][C:4]#[N:5].[NH2:13][C:14]([NH2:16])=[S:15].II>N1C=CC=CC=1>[NH2:16][C:14]1[S:15][C:3]([C:4]#[N:5])=[C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:13]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2723790ThioureaHCID 27589483-(3-Fluorophenyl)-3-oxopropanenitrile

Product 1

HCID 214555522-Amino-4-Phenylthiazole-5-carbonitrileYield 102.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

5 g (34.0 mmol) of 3-oxo-3-(3-fluorophenyl)-propanenitrile were dissolved in pyridine (30 ml) and thiourea (5 g, 68.0 mmol) and iodine (8.70 g, 34.40 mmol) were added successively. The solution was stirred at 100° C. for 12 h. The mixture was then cooled to room temperature and poured into ice-water (500 ml). The resulting solid was filtered, washed with water and recrystallized from ethanol to give 7.0 g (91%) of a yellow solid.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9481998b8e624a398465f90ae71b08f4
Source dataset
uspto-grants-2013_04
Patent number
US08410282B2

Reaction notes

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