Benzoyl isothiocyanate → 5-(3-Benzoyl-thioureido)-1-methyl-1H-imidazole-4-carboxylic acid amide

HRID 1588942Notes

Reaction equation

HRID 1588942 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]([NH2:10])=[O:9].[C:11]([N:19]=[C:20]=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:11]([NH:19][C:20]([NH:1][C:2]1[N:6]([CH3:7])[CH:5]=[N:4][C:3]=1[C:8]([NH2:10])=[O:9])=[S:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 64202875-Amino-1-methyl-1H-imidazole-4-carboxamide

Product 1

HCID 148971415-(3-Benzoyl-thioureido)-1-methyl-1H-imidazole-4-carboxylic acid amideYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Amino-1-methyl-1H-imidazole-4-carboxamide (6.5 g, 45 mM) and benzoylisothiocyanate (7.7 g, 47 mM) were refluxed in acetone (90 ml) for 4 hours under N2. After cooling in an ice bath the formed product was filtered off, washed with acetone and dried. Hereby was isolated 13.0 g (95%) of the title compound as a white powder, mp 194°-196° C.

Workup

  1. temperatureAfter cooling in an ice bath the formed product
  2. filtrationwas filtered off
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-53af0f7e8d0f4d2bb913e64a8b8e1b3e
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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