Hydrogen Sulfide → (3-Methylphenyl)ethanethioamide

HRID 1288242Notes

Reaction equation

HRID 1288242 reaction equation
[SH2:1].[CH3:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH2:11])=[S:1])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 76279m-Methylphenylacetonitrile

Product 1

HCID 21504242(3-Methylphenyl)ethanethioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulphide gas was passed through a solution of 3-methylphenylacetonitrile (26.2 g.) in dry pyridine (30 ml.) and triethylamine (20.2 g.) during 5 hours. The solution was allowed to stand at room temperature overnight and then evaporated under reduced pressure. The residue was dissolved in benzene and precipitated with light petroleum (b.p. 60°-80°). The product, m.p. 66°-69°, was recrystallised from a mixture of ethanol and water to give pure 3-methylphenyl(thioacetamide), m.p. 76°-78°.

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in benzene
  3. customprecipitated with light petroleum (b.p. 60°-80°)
  4. customThe product, m.p. 66°-69°, was recrystallised from a mixture of ethanol and water

Sources & evidence

ORD record
ord-dbb994dd55a34e92a3fa458032a07d4e
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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