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

HRID 570612Notes

Reaction equation

HRID 570612 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

Thiophosgene (10 g, 87.71 mmol) was dissolved in water and stirred at RT for 10 min. 4-Amino-2-trifluoromethyl-benzonitrile was added portionwise at RT. The reaction mixture was stirred at RT for 2 h. The product was extracted with DCM, the 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. stirringThe reaction mixture was stirred at RT for 2 h
  2. extractionThe product was extracted with DCM
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-4c6359b01b1a47d89aff74b444bee029
Source dataset
uspto-grants-2015_05
Patent number
US09023869B2

Reaction notes

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