Hydrogen Sulfide → Methyl 1-methylpyrrol-2-acetate

HRID 1703752Notes

Reaction equation

HRID 1703752 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=O)[C:8]([O:10][CH3:11])=[O:9].S>N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 402Hydrogen Sulfide2×HCID 22759895Methyl 1-methyl-α-oxo-1H-pyrrole-2-acetate

Product 1

HCID 103992Methyl 1-methylpyrrol-2-acetateYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
63 °C

Procedure

A solution of 50g of methyl 1-methylpyrrole-2-glyoxylate in 200 ml of pyridine is cooled to -78° C. and 64g of hydrogen sulfide is added. The mixture is sealed in a stirred autoclave and heated to 63° C. The pressure rises to about 130 p.s.i. After 27 hrs., the hydrogen sulfide is driven off in a nitrogen stream and the solution is decanted from the precipitated sulfur. Pyridine is distilled off at 20 mm Hg. The residue is distilled at 0.03 mm Hg, b.p. 68-70° C., to give 39.2g of oily methyl 1-methylpyrrole-2-acetate (86% yield).

Workup

  1. customThe mixture is sealed in a stirred autoclave
  2. customthe solution is decanted from the precipitated sulfur
  3. distillationPyridine is distilled off at 20 mm Hg
  4. distillationThe residue is distilled at 0.03 mm Hg, b.p. 68-70° C.

Sources & evidence

ORD record
ord-fc05f2eb207c43fca3530064e22b3743
Source dataset
uspto-grants-1978_11
Patent number
US04125537

Reaction notes

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