Formamide → 7-(Thiazol-4-yl)imidazo[5,1-b]thiazole

HRID 989852Notes

Reaction equation

HRID 989852 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]([NH2:17])=O.Cl[CH2:19][C:20]([C:22]1[N:23]=[CH:24][N:25]2[CH:29]=[CH:28][S:27][C:26]=12)=O.C(=O)([O-])O.[Na+]>ClCCl.O>[S:2]1[CH:19]=[C:20]([C:22]2[N:23]=[CH:24][N:25]3[CH:29]=[CH:28][S:27][C:26]=23)[N:17]=[CH:15]1

Participants

7

Reactant 4

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 234493337-Chloroacetylimidazo[5,1-b]thiazole

Product 1

HCID 234491117-(Thiazol-4-yl)imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Diphosphorus pentasulfide (846 mg) was added to 8.4 ml of formamide. The mixture was stirred at room temperature overnight. 7-Chloroacetylimidazo[5,1-b]thiazole (2.32 g) was added to the reaction solution. The mixture was stirred at room temperature for 15 hr. Water (20 ml) and 10 ml of dichloromethane were added thereto. The mixture was adjusted to pH 8.8 by gradually adding a sodium hydrogencarbonate powder. Extraction was carried out six times with 50 ml of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2) to give 1.72 g of 7-(thiazol-4-yl)imidazo[5,1-b]thiazole.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hr
  2. extractionExtraction
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-e361cbd926e242b0b2d4a3781f6243f7
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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