Thiophosgene → 4-Cyano-2,5-difluoro-phenyl isothiocyanate

HRID 1250433Notes

Reaction equation

HRID 1250433 reaction equation
[C:1]([C:3]1[C:9]([F:10])=[CH:8][C:6]([NH2:7])=[C:5]([F:11])[CH:4]=1)#[N:2].[C:12](Cl)(Cl)=[S:13]>C1(C)C=CC=CC=1>[C:1]([C:3]1[C:9]([F:10])=[CH:8][C:6]([N:7]=[C:12]=[S:13])=[C:5]([F:11])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 27359004-Amino-2,5-difluorobenzonitrile

Product 1

HCID 183261924-Cyano-2,5-difluoro-phenyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.0 g (65 mmol) of 4-cyano-2,5-difluoro-aniline are introduced into 100 ml of toluene and 8.2 g (71 mmol) of thiophosgene are slowly added to the mixture heated to 80° C. to 90° C. The reaction mixture is then refluxed for approximately 40 hours. Then, after the solvent has been carefully distilled off under reduced pressure, the product (4-cyano-2,5-difluoro-phenyl isothiocyanate) is obtained as an ochre colourant.

Workup

  1. additionare slowly added to the mixture
  2. temperatureheated to 80° C. to 90° C
  3. temperatureThe reaction mixture is then refluxed for approximately 40 hours
  4. distillationThen, after the solvent has been carefully distilled off under reduced pressure

Sources & evidence

ORD record
ord-ccbe2fe6b47046218ece3ff2a8b4e13e
Source dataset
uspto-grants-2002_01
Patent number
US06339044B1

Reaction notes

Loading…