Pyridine → 4-(Trifluoromethyl)phenyl isothiocyanate

HRID 659735Notes

Reaction equation

HRID 659735 reaction equation
[C:1](Cl)(Cl)=[S:2].[F:5][C:6]([F:15])([F:14])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.N1C=CC=CC=1>ClCCl>[N:13]([C:10]1[CH:11]=[CH:12][C:7]([C:6]([F:5])([F:14])[F:15])=[CH:8][CH:9]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 99644-(Trifluoromethyl)anilineHCID 10040Thiophosgene

Product 1

HCID 1371344-(Trifluoromethyl)phenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thiophosgene (5 mL) was added portion wise to a stirred solution of 4-trifluoromethyl-phenylamine (10 grams) and pyridine (12.5 mL) in dichloromethane (2 Liters) at 0° C. The reaction was maintained at the same temperature for 30 minutes. The reaction mixture was then diluted with dichloromethane and washed several times with a saturated solution of copper sulfate, followed by water, drying over sodium sulfate and evaporating to give the crude product which was further purified by passing through a column of silica gel, to yield the pure product (11 grams).

Workup

  1. temperatureThe reaction was maintained at the same temperature for 30 minutes
  2. washwashed several times with a saturated solution of copper sulfate
  3. dry with materialdrying over sodium sulfate
  4. customevaporating
  5. customto give the crude product which
  6. customwas further purified

Sources & evidence

ORD record
ord-8630bf42be8e4cfdb2d1d63699a67816
Source dataset
uspto-grants-2011_12
Patent number
US08080668B2

Reaction notes

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