Hydrochloric Acid → 4-(Trifluoromethyl)thiobenzamide

HRID 1295092Notes

Reaction equation

HRID 1295092 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.C(N)(=[S:15])C.Cl.O>CN(C=O)C>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([C:9]([NH2:10])=[S:15])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 67995Benzonitrile, 4-(trifluoromethyl)-HCID 2723949Thioacetamide

Product 1

HCID 27348234-(Trifluoromethyl)thiobenzamideYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A solution of α,α,α-trifluoro-p-tolunitrile (603.5 g, 3.53 mol) in dry DMF (2 L) under N2 was heated at 70° C. and the Thioacetamide (505 g, 1.9 eq.) was added. The reaction mixture was treated with HCl gas before 15 minutes and was stirred at 95° C. for 6 hours. This treatment was operated 3 times and the mixture was stirred at rt for 24 hours. After cooling at 0° C., water was added and the residue was extracted with diethyl ether (4*1 L). The organic layer was washed with water (3*1 L), dried over Na2SO4 and then evaporated off. The brownish powder was washed with pentane (3 L) to give the title compound (530.3 g, 2.59 mol) as brown solid in a 73% yield.

Workup

  1. stirringthe mixture was stirred at rt for 24 hours
  2. temperatureAfter cooling at 0° C.
  3. extractionthe residue was extracted with diethyl ether (4*1 L)
  4. washThe organic layer was washed with water (3*1 L)
  5. dry with materialdried over Na2SO4
  6. customevaporated off
  7. washThe brownish powder was washed with pentane (3 L)

Sources & evidence

ORD record
ord-459242eee1944dbf856b86af13b02692
Source dataset
uspto-grants-2007_07
Patent number
US07241793B2

Reaction notes

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