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

HRID 1839317Notes

Reaction equation

HRID 1839317 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-bce039e24e1c45d9ae4c5bc3e30871fc
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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