Thiophosgene → 4-Isothiocyanato-2-(trifluoromethyl)benzonitrile

HRID 2370351Notes

Reaction equation

HRID 2370351 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1>O>[N:5]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[C:8]([C:14]([F:15])([F:16])[F:17])[CH:7]=1)=[C:1]=[S:2]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 116155404-Isothiocyanato-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared according to General Method 6. Thiophosgene (10 g, 87.71 mmol) was dissolved in water and stirred at RT for 10 minutes. 4-Amino-2-trifluoromethyl-benzonitrile was added portion wise at RT. The reaction mixture was stirred at RT for 2 h. The product was extracted with dichloromethane, organic layer was washed with water and brine, dried over sodium sulphate and evaporated to obtain 12 g of 4-Isothiocyanato-2-trifluoromethyl-benzonitrile.

Workup

  1. customThe title compound was prepared
  2. stirringThe reaction mixture was stirred at RT for 2 h
  3. extractionThe product was extracted with dichloromethane, organic layer
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-49081486620e45fbbb46d01b3c69a98a
Source dataset
uspto-grants-2014_04
Patent number
US08710086B2

Reaction notes

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