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

HRID 339547Notes

Reaction equation

HRID 339547 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][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:4]1[S:3][C:2]2=[N:1][C:10]([C:12]3[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=3)=[CH:9][N:6]2[CH:5]=1

Participants

5

Reactant 3

HCID 668402-Bromo-4'-nitroacetophenoneHCID 3517702-Amino-5-methylthiazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 868202Imidazo[2,1-b]thiazole, 2-methyl-6-(4-nitrophenyl)-Yield 26.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-methylthiazole (0.24 g, 2.11 mmol) and 2-bromo-4′-nitroacetophenone (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 the residue dissolved in DCM (75 ml) and washed with water (30 ml), brine (30 ml) and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by flash chromatography (50:1 DCM/MeOH) to give the title compound (0.143 g, 26%) 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
  6. dissolutionthe residue dissolved in DCM (75 ml)
  7. washwashed with water (30 ml), brine (30 ml)
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by flash chromatography (50:1 DCM/MeOH)

Sources & evidence

ORD record
ord-276f6fa674734d2889954d28cb2bdd21
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

Loading…