4-(Trifluoromethyl)benzamide → 4-(Trifluoromethyl)thiobenzamide

HRID 1742890Notes

Reaction equation

HRID 1742890 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:23])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 746844-(Trifluoromethyl)benzamideHCID 87949Lawesson's reagent

Product 1

HCID 27348234-(Trifluoromethyl)thiobenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-trifluoromethylbenzamide (79 mM) and Lawesson's reagent (39 mM) in toluene (200 mL) was heated at reflux for 4 hours under N2. The reaction mixture was cooled and the resulting precipitate was isolated by filtration to give 4-trifluoromethylthiobenzamide as a solid: mp 125° C. (The following general procedure was used to synthesize the various substituted thiobenzamides (Tetrahedron 35,2433, (1979)):

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours under N2
  3. temperatureThe reaction mixture was cooled
  4. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-492d5f40d4ba43ef87ff13b54b9e01ed
Source dataset
uspto-grants-1994_08
Patent number
US05342851

Reaction notes

Loading…