Methyl iodide → Methyl 1-methyl-4-(methylsulfanyl)-1H-pyrrole-2-carboxylate

HRID 1388925Notes

Reaction equation

HRID 1388925 reaction equation
[C:1]([S:3][C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[N:7]([CH3:9])[CH:8]=1)#N.CI.C[O-].[Na+]>CO>[CH3:13][O:12][C:10]([C:6]1[N:7]([CH3:9])[CH:8]=[C:4]([S:3][CH3:1])[CH:5]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 20469121Methyl 1-methyl-4-(thiocyanato)-1H-pyrrole-2-carboxylate

Product 1

HCID 13345725Methyl 1-methyl-4-(methylsulfanyl)-1H-pyrrole-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Cyanothio-2-methoxycarbonyl-1-methylpyrrole (2.8 g, 14.3 mmol) is dissolved in 50 ml of methanol under nitrogen. Methyliodide (1.25 ml, 20 mmol) is added followed by 1.08 g (20 mmole) of sodium methoxide. After stirring for about 30 minutes at room temperature, the reaction mixture is concentrated to a paste and then diluted with 100 ml of ethylether. The resulting precipitate is filtered off and the filtrate concentrated to give an oil which is distilled at 100° to 104° at 0.25 mm-Hg to afford 2.2 g (86%) of 2-methoxycarbonyl-4-methylthio-1-methylpyrrole.

Workup

  1. concentrationthe reaction mixture is concentrated to a paste
  2. additiondiluted with 100 ml of ethylether
  3. filtrationThe resulting precipitate is filtered off
  4. concentrationthe filtrate concentrated
  5. customto give an oil which
  6. distillationis distilled at 100° to 104° at 0.25 mm-Hg

Sources & evidence

ORD record
ord-f1eb8c74659848ad9c68267343a919f7
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

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