Methanol → HCID 14897149, compound

HRID 1588943Notes

Reaction equation

HRID 1588943 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][O:11]C(=O)C)[CH:5]=[N:4][C:3]=1[C:15]([NH2:17])=[O:16].C([N:26]=[C:27]=[S:28])(=O)C1C=CC=CC=1.CO.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O.C(O)(=O)C>[OH:11][CH2:10][CH2:9][O:8][CH2:7][N:6]1[C:2]([NH:1][C:27](=[S:28])[NH2:26])=[C:3]([C:15]([NH2:17])=[O:16])[N:4]=[CH:5]1

Participants

8

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 140640202-[(5-Amino-4-carbamoyl-1H-imidazol-1-yl)methoxy]ethyl acetate

Product 1

HCID 14897149HCID 14897149, compoundYield 83.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

5-Amino-1-[[2-(acetyloxy)ethoxy]methyl]-1H-imidazole-4-carboxamide (44.0 g, 182 mM) and benzoylisothiocyanate (29.7 g, 182 mM) were refluxed in acetone (430 ml) for 1 hour. To the resulting solution were added methanol (430 ml) and potassium carbonate (14.9 g, 108 mM) dissolved in water (45 ml) whereafter the mixture was refluxed for 4 hours. After cooling to room temperature acetic acid was added to a pH-value of 8. The formed product was filtered off at 0° C., washed and dried. Hereby 39.2 g (83%) of the title compound was isolated as a white powder, mp. 181°-182° C. (dec.). A sample crystallized from water had mp. 182°-183° C. (dec.). 13C-NMR(DMSO-d6) δppm: 183.9; 163.7; 134.9; 129.3; 127.9; 74.0; 70.4; 59.7.

Workup

  1. temperaturewas refluxed for 4 hours
  2. additionwas added to a pH-value of 8
  3. filtrationThe formed product was filtered off at 0° C.
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-31ead809b0234f548ae5747e1bb39aad
Source dataset
uspto-grants-1993_06
Patent number
US05223619

Reaction notes

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