Hydrogen Sulfide → 1,5-Dimethyl-1H-pyrrole-2-carbothioamide

HRID 1860472Notes

Reaction equation

HRID 1860472 reaction equation
[C:1]([C:3]1[N:4]([CH3:9])[C:5]([CH3:8])=[CH:6][CH:7]=1)#[N:2].C(N(CC)CC)C.[SH2:17]>C(O)C>[CH3:9][N:4]1[C:5]([CH3:8])=[CH:6][CH:7]=[C:3]1[C:1](=[S:17])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 918121,5-Dimethylpyrrole-2-carbonitrile

Product 1

HCID 150762371,5-Dimethyl-1H-pyrrole-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 g of 2-cyano-1,5-dimethylpyrrol are dissolved in 40 ml of ethanol and treated with 10 ml of triethylamine. 50 ml of an ethanolic H2S solution (3.8 g/100 ml) are added and the mixture is heated for ca. 15 hours in an autoclave at 70°. The reaction mixture is cooled and the solvent is evaporated off to obtain ca. a quarter of its volume. 1,5-dimethylpyrrol-2-carbothioamide crystallizes upon cooling at 0° in the form of a light yellow precipitate.

Workup

  1. temperaturethe mixture is heated for ca. 15 hours in an autoclave at 70°
  2. temperatureThe reaction mixture is cooled
  3. customthe solvent is evaporated off
  4. customto obtain ca. a quarter of its volume
  5. custom1,5-dimethylpyrrol-2-carbothioamide crystallizes
  6. temperatureupon cooling at 0° in the form of a light yellow precipitate

Sources & evidence

ORD record
ord-bf907958d34144bbac9ee7c2f55dffb3
Source dataset
uspto-grants-2003_03
Patent number
US06531465B1

Reaction notes

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