Methyl iodide → Dimethyl 2-(methylthio)-1-phenyl-4,5-imidazoledicarboxylate

HRID 1728954Notes

Reaction equation

HRID 1728954 reaction equation
[CH3:1][O-].[Na+].[SH:4][C:5]1[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]([C:15]([O:17][CH2:18]C)=[O:16])=[C:8]([C:10]([O:12][CH2:13]C)=[O:11])[N:9]=1.IC>CO>[CH3:1][S:4][C:5]1[N:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]([C:15]([O:17][CH3:18])=[O:16])=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10942334Sodium MethoxideHCID 178470333HCID 178470333, compound

Product 1

HCID 14416592Dimethyl 2-(methylthio)-1-phenyl-4,5-imidazoledicarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1.8 g; 0.033 mol) was slowly added to a suspension of diethyl 2-mercapto-1-phenyl-4,5-imidazoledicarboxylate (10 g; 0.031 mol) in absolute methanol (100 mL) then iodomethane (5 g; 0.035 mol) was added. The mixture was allowed to stir overnight, additional iodomethane (5 g; 0.035 mol) was added and the mixture was stirred for 1 hour. The methanol was removed in vacuo and ice-cold water was added to the residue. The mixture was filtered, the collected solid was washed with water and dried to give 7.6 g (80%) of pure dimethyl 2-(methylthio)-1-phenyl-4,5-imidazoledicarboxylate (mp 121°-122° C).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customThe methanol was removed in vacuo and ice-cold water
  3. additionwas added to the residue
  4. filtrationThe mixture was filtered
  5. washthe collected solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-7b7ec5f26b5741549b22ac325edff6ef
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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