4-Fluorobenzamide → 4-Fluorothiobenzamide

HRID 651385Notes

Reaction equation

HRID 651385 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:20])=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 715724-FluorobenzamideHCID 87949Lawesson's reagent

Product 1

HCID 7372234-FluorothiobenzamideYield 146.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Fluorobenzamide (5.0 g, 35.9 mmol) in benzene (100 ml) is added Lawesson's reagent (7,27 g, 18.0 mmol) and the resulting solution is heated to reflux for 1 hour. The solution is cooled to room temperature, concentrated and water (150 ml) added. The mixture is heated to reflux for 3 hours, and cooled to room temperature. The precipitate is filtered and dried under vacuum to yield 4-fluorothiobenzamide as a yellow solid (4.1 g, 71%). 1H NMR (CDCl3): δ 7.09 (t, 2H), 7.90(dd, 2H).

Workup

  1. temperaturethe resulting solution is heated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated
  4. additionwater (150 ml) added
  5. temperatureThe mixture is heated
  6. temperatureto reflux for 3 hours
  7. temperaturecooled to room temperature
  8. filtrationThe precipitate is filtered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-5c331d9c8987460a9fa17b06266ed3ab
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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