Hydrogen Sulfide → 4-Chlorothiobenzamide

HRID 2106995Notes

Reaction equation

HRID 2106995 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[SH2:10].O>N1C=CC=CC=1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[S:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 962WaterHCID 121634-Chlorobenzonitrile

Product 1

HCID 27348264-Chlorothiobenzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

68.8 g (0.5 mol) of 4-chlorobenzonitrile were dissolved in a mixture of 100 ml pyridine and 50 ml triethylamine. Whilst stirring, an even flow of 15 l (0.67 mol/hour) of hydrogen sulphide was introduced at room temperature, then 11 l (0.5 mol/hour) for 30 min at 50° C., i.e. a total of 1.25 mol. This was then stirred for a further 30 min at 50° C. and then mixed into 1.5 liters of water. The crystallate was drawn off, washed with plenty of water and dried,

Workup

  1. stirringThis was then stirred for a further 30 min at 50° C.
  2. washwashed with plenty of water
  3. customdried

Sources & evidence

ORD record
ord-3ceaed9c3f5f4cafb38cbe3fd93702f7
Source dataset
uspto-grants-1990_06
Patent number
US04933328

Reaction notes

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