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

HRID 1393737Notes

Reaction equation

HRID 1393737 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, 2.1 g of ethyl 2-aminothiazole-4-carboxylate (Combi-Blocks, 0.0123 mol) was mixed with 25 mL of methyl ethyl ketone 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 (MS, M++H=318).

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-e795564406274b8f8f6d2a682daa549d
Source dataset
uspto-grants-2008_03
Patent number
US07345178B2

Reaction notes

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