Acetone → 1-Methyl-5-thioureido-1H-imidazole-4-carboxamide

HRID 1588944Notes

Reaction equation

HRID 1588944 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[N:17]([CH3:18])[CH:16]=[N:15][C:14]=1[C:19]([NH2:21])=[O:20])=[S:11])(=O)C1C=CC=CC=1.CC(C)=O.CO.C(=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C>[CH3:18][N:17]1[C:13]([NH:12][C:10](=[S:11])[NH2:9])=[C:14]([C:19]([NH2:21])=[O:20])[N:15]=[CH:16]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 11430Potassium CarbonateHCID 148971415-(3-Benzoyl-thioureido)-1-methyl-1H-imidazole-4-carboxylic acid amide

Product 1

HCID 148971451-Methyl-5-thioureido-1H-imidazole-4-carboxamideYield 96.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

5-(N'-benzoylthiocarbamoyl)amino-1-methyl-1H-imidazole-4-carboxamide (12.1 g, 40 mM) was added to a mixture of acetone and methanol (1:1) (200 ml). Potassium carbonate 2.8 g, 20 mM) dissolved in water (12 ml) was added. The reaction mixture was refluxed under N2 for 6 hours whereafter acetic acid (2.9 g, 48 mM) was added. After stirring in an ice bath the product was filtered off, washed and dried. Hereby was isolated 7.7 g (96%) of the title compound as a white powder, mp. 270°-274° C. (dec.) (the conversion begins at about 220° C.).

Workup

  1. additionwas added
  2. additionwas added
  3. filtrationwas filtered off
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-732d9a7c40c54724a344028f6849feab
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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