Hydrogen Sulfide → 4-Carbamothioylbenzoic acid

HRID 1445953Notes

Reaction equation

HRID 1445953 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[SH2:19].O>N1C=CC=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)(=[S:19])[NH2:2]

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 962WaterHCID 8471TriethylamineHCID 120874-Cyanobenzoic acid

Product 1

HCID 167725014-Carbamothioylbenzoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3 g of 4-cyanobenzoic acid 1 (20.4 mmol) were dissolved in 40 mL of pyridine and 2.1 mL of triethylamine (20.4 mmol) were added. Dry hydrogen sulphide was passed through the solution in a steady steam for 4 h. The mixture was then poured into water and the solid collected by filtration. Recrystallization from petroleum ether furnished 2.51 g of the pure compound 2 (68% yield).

Workup

  1. filtrationthe solid collected by filtration
  2. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-bb82525e69394ee0aba5ed6b5012d7e8
Source dataset
uspto-grants-2010_02
Patent number
US07666907B2

Reaction notes

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