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

HRID 244963Notes

Reaction equation

HRID 244963 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[C:14](Cl)(Cl)=[S:15]>O>[N:1]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1)=[C:14]=[S:15]

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

4-Amino-2-trifluoromethylbenzonitrile, (2.23 g, 12 mmol) was added portionwise over 15 minutes into the well-stirred heterogeneous mixture of thiophosgene (1 ml, 13 mmol) in water (22 ml) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3×15 ml). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product, 4-isothiocyanato-2-trifluoromethylbenzonitrile, (1a), as brownish solid and was used as such for the next step (232 g, 11.9 mmol, 99%).

Workup

  1. extractionThe reaction medium was extracted with chloroform (3×15 ml)
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e52357840c594bc0a056885ee24ef372
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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