Water → 2-Amino-4-phenylthiazole

HRID 231546Notes

Reaction equation

HRID 231546 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:11][C:12]([NH2:14])=[S:13].O>CO>[NH2:14][C:12]1[S:13][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 2723790Thiourea

Product 1

HCID 403022-Amino-4-phenylthiazoleYield 85.15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 19.9 g (0.10 mol) of α-bromo-acetophenone and 11.4 g (0.15 mol) of thiourea in 75 ml of methanol is refluxed for 2 h. It is evaporated to dryness under reduced pressure and the evaporation residue is taken up with water. The resulting solution, heated to the reflux temperature, is treated with CXA charcoal and then rendered alkaline with aqueous ammonia. The precipitate formed is isolated by filtration and purified by recrystallization from isopropanol, with CXA charcoal treatment. to give 15 g (yield: 85.15%) of the expected product in the form of water-insoluble white needles. M.p. (inst.)=150° C.

Workup

  1. customIt is evaporated to dryness under reduced pressure
  2. temperatureThe resulting solution, heated to the reflux temperature
  3. additionis treated with CXA charcoal
  4. customThe precipitate formed
  5. customis isolated by filtration
  6. custompurified by recrystallization from isopropanol, with CXA charcoal treatment

Sources & evidence

ORD record
ord-c7e2722c24ed4f17a5955e331ecbdc30
Source dataset
uspto-grants-1989_07
Patent number
US04847274

Reaction notes

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