Hydrogen Sulfide → 4-Fluorothiobenzamide

HRID 1154889Notes

Reaction equation

HRID 1154889 reaction equation
N1C=CC=CC=1.[SH2:7].[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.C(N(CC)CC)C>O>[F:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]([NH2:14])=[S:7])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 1049PyridineHCID 8471TriethylamineHCID 145174-Fluorobenzonitrile

Product 1

HCID 7372234-Fluorothiobenzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Eighty-five ml of dry pyridine was saturated with hydrogen sulfide. To this was added 25 g of p-fluorobenzonitrile and 33 ml of triethylamine. Hydrogen sulfide was passed through the solution at room temperature, with good stirring. After 4 hours a sample on thin layer chromatography showed no nitrile. The solution was poured into water (600 ml) and ice. The solid product was filtered, washed with water and dried. Yield of 27.3 g, mp 143°--145° C.

Workup

  1. customwas passed through the solution at room temperature, with good stirring
  2. filtrationThe solid product was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1c06bdb0642c47c2acf818e819e8465b
Source dataset
uspto-grants-1981_11
Patent number
US04298743

Reaction notes

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