2-Bromo-1-(3-nitrophenyl)ethan-1-one → 2-Amino-4-(3-nitrophenyl)thiazole

HRID 737151Notes

Reaction equation

HRID 737151 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C([O-])(=O)C.[Na+].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)=O>C(O)C>[N+:20]([C:16]1[CH:15]=[C:14]([C:12]2[N:1]=[C:2]([NH2:4])[S:3][CH:11]=2)[CH:19]=[CH:18][CH:17]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 517045Sodium AcetateHCID 2723790Thiourea

Product 1

HCID 6135042-Amino-4-(3-nitrophenyl)thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.31 g, 4.1 mmol) and sodium acetate (0.44 g, 5.3 mmol) were combined in 30 mL of dry ethanol. To this suspension was added 2-bromo-1-(3-nitro-phenyl)-ethanone (1.0 g, 4.1 mmol). Reaction mixture was stirred at room temperature overnight. Reaction mixture was evaporated to dryness to yield 4-(3-nitro-phenyl)-thiazol-2-ylamine, which was used in the next step without any further purification. MS: 222.0 (M+H+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. customwas evaporated to dryness

Sources & evidence

ORD record
ord-f7662110da014159a7bae5deff1ab0bd
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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