Chloroform → 4-(Trifluoromethyl)phenyl isothiocyanate

HRID 747533Notes

Reaction equation

HRID 747533 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.[C:12](Cl)(Cl)=[S:13].C(=O)([O-])O.[Na+].C(Cl)(Cl)Cl>O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:9]=[CH:8][C:6]([N:7]=[C:12]=[S:13])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 99644-(Trifluoromethyl)anilineHCID 10040ThiophosgeneHCID 516892Sodium Bicarbonate

Product 1

HCID 1371344-(Trifluoromethyl)phenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(Trifluoromethyl)aniline (1.34 g), thiophosgen (0.73 ml), sodium hydrogen carbonate (5.1 g), chloroform (70 ml) and water (140 ml) were treated by the method disclosed in the literature (Burke, T. R., Jr.; Bajwa, B. S.; Jacobson, A. E.; Rice, K. C.; Streaty, R. A.; Klee, W. A. J. Med. Chem., 1984, 27, 1570-1574) to give the title compound (1.62 g).

Sources & evidence

ORD record
ord-a3fe95618a5741f58077a0cda1964041
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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