Methyl iodide → Diethyl 2-(methylsulfanyl)-1H-imidazole-4,5-dicarboxylate

HRID 1728960Notes

Reaction equation

HRID 1728960 reaction equation
I[CH3:2].[SH:3][C:4]1[NH:5][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:8]=1.C[O-].[Na+]>CO>[CH3:2][S:3][C:4]1[NH:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10942334Sodium MethoxideHCID 178470336HCID 178470336, compound

Product 1

HCID 14416595Diethyl 2-(methylsulfanyl)-1H-imidazole-4,5-dicarboxylateYield 86.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodomethane (15.62 g; 0.11 mol) was added to a solution of 24.4 g (0.10 mol) of the above-produced diethyl 2-mercapto-4,5-imidazole-dicarboxylate (24.4 g; 0.10 mol) and sodium methoxide (6.0; 0.11 mol) in absolute methanol (500 mL) at room temperature. Additional iodomethane (5 g) was added after 1 hour and the yellow solution was allowed to stir at room temperature for 3 hours. The methanol was then removed in vacuo, the residue was treated with cold water and the light yellow solid was filtered and dried to give diethyl 2-(methylthio)imidazole-4,5-dicarboxylate (22.3 g; 86%).

Workup

  1. customThe methanol was then removed in vacuo
  2. additionthe residue was treated with cold water
  3. filtrationthe light yellow solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-475bf17bb9684810b9bd05e89f46f2ce
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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