4-(Trifluoromethyl)aniline → N-[4-(Trifluoromethyl)phenyl]thiourea

HRID 1816177Notes

Reaction equation

HRID 1816177 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[S-:12][C:13]#[N:14].[K+]>Cl>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:13]([NH2:14])=[S:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 516872Potassium thiocyanate

Product 1

HCID 2777727N-[4-(Trifluoromethyl)phenyl]thiourea

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-Trifluoromethylaniline (2.00 g; 12.4 mmol) and potassium thiocyanate (4.82 g; 49.7 mmol) was suspended in 1N aqueous HCl (20 ml). A clear solution was obtained upon heating to reflux (after 1 hour, a precipitate started to form). The mixture was refluxed overnight, then cooled to room temperature and extracted with ethyl acetate. The organic phase was washed with brine and dried with anhydrous sodium sulphate. Solvent was removed, and the residual oil was striped twice from acetonitril, to give a quantitative yield of (4-trifluoromethylphenyl)thiourea.

Workup

  1. customA clear solution was obtained
  2. temperatureupon heating
  3. temperatureto reflux (after 1 hour
  4. customto form)
  5. temperatureThe mixture was refluxed overnight
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried with anhydrous sodium sulphate
  9. customSolvent was removed

Sources & evidence

ORD record
ord-7a74adb38eb743e89d12fabd00f9353d
Source dataset
uspto-grants-2005_04
Patent number
US06881746B2

Reaction notes

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