2-Aminothiazole → Imidazo[2,1-b]thiazole,5-[4-(methylsulfonyl)phenyl]-6-phenyl-

HRID 741682Notes

Reaction equation

HRID 741682 reaction equation
[C:1]1([C:7](=O)[CH:8](Br)[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])(O)=O.[Na+]>CCO>[CH3:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]2[N:26]3[C:22]([S:23][CH:24]=[CH:25]3)=[N:21][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 516892Sodium BicarbonateHCID 153152121-Phenyl-2-bromo-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 9928539Imidazo[2,1-b]thiazole,5-[4-(methylsulfonyl)phenyl]-6-phenyl-Yield 44.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the bromoketone of step 3 (2.26 g, 6.4 mmol) and 2-aminothiazole (964 mg, 9.6 mmol) in EtOH (45 mL) was heated to reflux for 18 h. Aqueous NaHCO3 was added to the cooled mixture and the mixture was extracted with Et2O. The Et2O extracts were washed with brine, dried over MgSO4, filtered and concentrated to an oil. Chromatography of the oil on silica gel (eluted with 60 % EtOAc/hexane) gave 1 g (44%) of the title compound: m.p. 190°-192° C. Anal. calcd for C18H14N2O2S2 : C, 61.00; H, 3.98; N, 7.90. Found: C, 60.31; H, 3.96; N, 7.68. 1H NMR (CD3COCD3): δ3.20 (s, 3H), 7.20-7.34 (m, 4H), 7.58-7.61 (m, 2H), 7.77-7.83 (m, 3H), 8.03-8.06 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. extractionthe mixture was extracted with Et2O
  4. washThe Et2O extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-cb075af8373741bc90c99770b980ef22
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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