Ethyl 2-aminothiazole-4-carboxylate → Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylate

HRID 888242Notes

Reaction equation

HRID 888242 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=O>C(C(C)=O)C>[CH2:10]([O:9][C:7]([C:5]1[N:6]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])[N:1]=[C:2]2[S:3][CH:4]=1)=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 2440252-Bromo-2'-nitroacetophenone

Product 1

HCID 25232522Ethyl 6-(2-nitrophenyl)imidazo[2,1-b]thiazole-3-carboxylateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In a typical run, ethyl 2-aminothiazole-4-carboxylate (2.1 g, 0.0123 mol) was taken up in methyl ethyl ketone (25 mL) along with 2-bromo-2′-nitroacetophenone (3.0 g, 0.0123 mol). The reaction mixture was stirred under reflux for 18 hours. It was then cooled to room temperature and filtered to remove some of the solids. The filtrate was concentrated to afford 3.10 g of 6-(2-nitro-phenyl)-imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (Calc'd for C14H12N3O4S: 318.3, [M+H]+ found: 319).

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationfiltered
  3. customto remove some of the solids
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e4c2028e77b44271803e8714b78af284
Source dataset
uspto-grants-2012_08
Patent number
US08247565B2

Reaction notes

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