Ethyl Acetate → 2-Amino-4-(3-nitrophenyl)thiazole

HRID 2086768Notes

Reaction equation

HRID 2086768 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[NH2:14][C:15]([NH2:17])=[S:16].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:17][C:15]1[S:16][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=2)[N:14]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 516892Sodium BicarbonateHCID 2723790Thiourea

Product 1

HCID 6135042-Amino-4-(3-nitrophenyl)thiazoleYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-3′-nitroacetophenone (12.2 g) and thiourea (3.81 g) in ethanol (100 ml) was stirred at room temperature for 15 minutes. The reaction mixture was poured into a mixture of ethyl acetate and an aqueous sodium bicarbonate solution. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-amino-4-(3-nitrophenyl)thiazole (10.21 g).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resultant solid was collected
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-1758c215c163452f981e9b597dfc7710
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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