Phenacyl bromide → 2-Amino-4-phenylthiazole

HRID 2358031Notes

Reaction equation

HRID 2358031 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[NH2:11][C:12]([NH2:14])=[S:13]>C(O)C>[C:4]1([C:2]2[N:11]=[C:12]([NH2:14])[S:13][CH:1]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 2723790Thiourea

Product 1

HCID 403022-Amino-4-phenylthiazoleYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2 g of phenacylbromide and 0.76 g of thiourea in 50 mL ethanol was refluxed overnight. After solvent evaporation, the residue was redissolved in 50 mL DCM and treated by 50 mL of a 2% sodium carbonate solution in water. The organic layer was dried and evaporated to yield 1.45 g (82%) of 4-phenyl-2-thiazolamine (intermediate p. Mass spectral data: m/z=177 (M+H).

Workup

  1. temperaturewas refluxed overnight
  2. customAfter solvent evaporation
  3. dissolutionthe residue was redissolved in 50 mL DCM
  4. additiontreated by 50 mL of a 2% sodium carbonate solution in water
  5. customThe organic layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-8ab7c3e46ae640af8946d02a5ab527df
Source dataset
uspto-grants-2010_07
Patent number
US07763641B2

Reaction notes

Loading…