Benzoyl isothiocyanate → HCID 24855566, compound

HRID 912713Notes

Reaction equation

HRID 912713 reaction equation
C(N=[C:10]=[S:11])(=O)C1C=CC=CC=1.[CH3:12][C:13]1[C:17]([CH2:18][NH:19][C:20]2[N:21]=[CH:22][NH:23][C:24]=2[C:25]([NH2:27])=[O:26])=[C:16]([CH3:28])[O:15][N:14]=1>CC(C)=O>[CH3:12][C:13]1[C:17]([CH2:18][N:19]2[C:20]3[N:21]=[CH:22][NH:23][C:24]=3[C:25](=[O:26])[NH:27][C:10]2=[S:11])=[C:16]([CH3:28])[O:15][N:14]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67415024HCID 67415024, compound

Product 1

HCID 24855566HCID 24855566, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl isothiocyanate (0.62 mL, 4.64 mmol) was added, dropwise, to a solution of 4-{[(3,5-dimethylisoxazol-4-yl)methyl]amino}-1H-imidazole-5-carboxamide (0.91 g, 3.86 mmol, obtained from Example 21(a)) in acetone (20 mL). After stirring o.n., the solvent was evaporated in vacuo and the residue triturated with dichloromethane. The solid was removed by filtration and the filtrate was concentrated in vacuo. A solution of ammonia in methanol (7 N, 20 mL) was added to the resulting residue and this solution was transferred to a sealable tube. The vessel was sealed and placed in an 80° C. oil bath for 3 h. After cooling to r.t., the solution was concentrated in vacuo. The product was purified by recrystallization from DMSO/water, filtered and triturated sequentially with water, methanol and dichloromethane, providing the title compound (0.10 g, 10% yield) as a solid.

Workup

  1. custom, the solvent was evaporated in vacuo
  2. customthe residue triturated with dichloromethane
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionA solution of ammonia in methanol (7 N, 20 mL) was added to the resulting residue
  6. customthis solution was transferred to a sealable tube
  7. customThe vessel was sealed
  8. customplaced in an 80° C.
  9. customfor 3 h
  10. concentrationthe solution was concentrated in vacuo
  11. customThe product was purified by recrystallization from DMSO/water
  12. filtrationfiltered
  13. customtriturated sequentially with water, methanol and dichloromethane

Sources & evidence

ORD record
ord-c3fcbdbaa2ff4480afa3227b397eb08e
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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