Phosphorus oxychloride → Imidazo[5,1-b][1,3]thiazole-7-carbonitrile

HRID 382597Notes

Reaction equation

HRID 382597 reaction equation
[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[CH:10][S:9][C:8]=12)(=O)[NH2:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([C:4]1[N:5]=[CH:6][N:7]2[CH:11]=[CH:10][S:9][C:8]=12)#[N:2]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 18359792Imidazo[5,1-b]thiazole-7-carboxamide

Product 1

HCID 18360001Imidazo[5,1-b][1,3]thiazole-7-carbonitrileYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 997 mg of 7-carbamoylimidazo[5,1-b]-thiazole in 80 ml of dichloromethane were add under ice-cooling 7.28 ml of N,N-diisopopylethylamine and 2.23 ml of phosphorus oxychloride. After the reaction mixture was stirred at the same temperature, it was poured onto ice-water, adjusted pH to 7.5 with aqueous sodium hydrogen carbonate, and extracted three times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography on silica gel (dichloromethane:methanol=15:1) to give 871 mg of 7-cyanoimidazo[5,1-b]thiazole.

Workup

  1. additionwere add under ice-
  2. additionwas poured onto ice-water
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography on silica gel (dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-5e787187a85d481fb2b93a74c23a4ba9
Source dataset
uspto-grants-2001_10
Patent number
US06310056B1

Reaction notes

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