2-(Trifluoromethyl)aniline → 2-(Trifluoromethyl)phenyl isothiocyanate

HRID 1744206Notes

Reaction equation

HRID 1744206 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[C:12](Cl)(Cl)=[S:13].C(OCC)(=O)C>O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[N:5]=[C:12]=[S:13]

Participants

5

Reactant 3

HCID 69222-(Trifluoromethyl)anilineHCID 8857Ethyl AcetateHCID 10040Thiophosgene

Product 1

HCID 7371622-(Trifluoromethyl)phenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-trifluoromethylaniline (4.1 ml, 0.0325 mol) is added dropwise at a temperature close to 20° C. and under an argon atmosphere to a mixture containing thiophosgene (2.5 ml, 0.0326 mol) in 43 ml of water. Agitation is carried out for twelve hours then 30 ml of ethyl acetate is added. The organic phase is extracted with water then with a solution of 10% sodium bicarbonate and finally with a solution of salt water. The organic phase is dried over magnesium sulphate and the solvent is evaporated off with a rotary evaporator. The product obtained (6.85 g, 100%) is in the form of a brown oil which is used immediately for the following reaction.

Workup

  1. customclose to 20° C. and under an argon atmosphere to a mixture
  2. waitAgitation is carried out for twelve hours
  3. extractionThe organic phase is extracted with water
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. customthe solvent is evaporated off with a rotary evaporator
  6. customThe product obtained (6.85 g, 100%)
  7. customis used immediately for the following reaction

Sources & evidence

ORD record
ord-f07156a3ec2e470abf4e8d3f91fb829b
Source dataset
uspto-grants-2006_03
Patent number
US07015213B1

Reaction notes

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