Methanol → HCID 15165839, compound

HRID 2372284Notes

Reaction equation

HRID 2372284 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=[C:3]1[SH:19].Cl[CH2:21][C:22](=[O:24])[CH3:23].C(N(CC)CC)C.CO>CC(C)=O.C(OCC)(=O)C.C(Cl)Cl>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:4]=[C:3]1[S:19][CH2:21][C:22](=[O:24])[CH3:23]

Participants

8

Reactant 4

HCID 887MethanolHCID 6571Chloroacetone2×HCID 8471Triethylamine2×HCID 178481672HCID 178481672, compound

Product 1

HCID 15165839HCID 15165839, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 1-methyl-4,5-diphenylimidazol-2-thiol (0.618 g, 0.00255 mol) was dissolved in 150 milliliters of acetone and to it was added with stirring 0.236 gram (0.00255 mol) of chloroacetone and 0.258 g (0.00255 mol) of triethylamine. The mixture was stirred overnight at room temperature. Since the reaction was not complete as determined by TLC, 0.25 gram of chloroacetone and 0.26 gram of triethylamine was added and the mixture refluxed for one hour. The mixture was then allowed to cool and evaporated in vacuo to obtain a residue. The latter was dissolved in ethyl acetate, the ethyl acetate solution was washed with water, 5% sodium hydroxide and brine, the washed solution was dried (MgSO4), and the dried solution evaporated in vacuo to obtain a still impure product. The latter was put over a silica gel column and developed with 1 percent methanol in methylene chloride to recover from the eluate after evaporating off the solvent, 0.561 gram of 1-methyl-4,5-diphenyl-2[(2-oxo-propyl)thio]imidazole. The product after recrystallization from isopropyl alcohol-hexane had a melting point of 179°-182° C.

Workup

  1. additionwas added
  2. additionwas added
  3. temperaturethe mixture refluxed for one hour
  4. temperatureto cool
  5. customevaporated in vacuo
  6. customto obtain a residue
  7. washthe ethyl acetate solution was washed with water, 5% sodium hydroxide and brine
  8. dry with materialthe washed solution was dried (MgSO4)
  9. customthe dried solution evaporated in vacuo
  10. customto obtain a still impure product
  11. customto recover from the eluate
  12. customafter evaporating off the solvent, 0.561 gram of 1-methyl-4,5-diphenyl-2[(2-oxo-propyl)thio]imidazole
  13. customThe product after recrystallization from isopropyl alcohol-hexane

Sources & evidence

ORD record
ord-c2e07649b46248e7882cb4a97dd89f68
Source dataset
uspto-grants-1992_03
Patent number
US05098707

Reaction notes

Loading…