2-Bromo-4'-nitroacetophenone → Imidazo[2,1-b]thiazole, 3-methyl-6-(4-nitrophenyl)-

HRID 339549Notes

Reaction equation

HRID 339549 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[CH3:7][C:5]1[N:6]2[CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)[N:1]=[C:2]2[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 668402-Bromo-4'-nitroacetophenoneHCID 741432-Amino-4-methylthiazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 3926234Imidazo[2,1-b]thiazole, 3-methyl-6-(4-nitrophenyl)-Yield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-methylthiazole (0.24 g, 2.11 mmol) and 2-bromo-4′-nitroaceto phenone (0.5 g, 2.05 mmol) in EtOH (20 ml) was heated under reflux for 16 h. The reaction mixture was allowed to cool and sodium bicarbonate (200 mg, 2.38 mmol) was added and heating was continued for 1 h. On cooling to room temperature, the solvent was removed under reduced pressure and DCM (75 ml) was added to the residue. The insoluble material was collected by filtration and purified by flash chromatography (50:1 DCM/MeOH) to give the title compound (0.266 g, 50%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. temperatureto cool
  4. temperatureheating
  5. customthe solvent was removed under reduced pressure and DCM (75 ml)
  6. additionwas added to the residue
  7. filtrationThe insoluble material was collected by filtration
  8. custompurified by flash chromatography (50:1 DCM/MeOH)

Sources & evidence

ORD record
ord-d22ea87459b945eaaca7131f0a61ac9b
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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