Thiophosgene → 3-Chloro-4-isothiocyanato-benzonitrile

HRID 2407517Notes

Reaction equation

HRID 2407517 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[Cl:14]>O>[Cl:14][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:6]=1[N:5]=[C:1]=[S:2])[C:10]#[N:11]

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 5198964-Amino-3-chlorobenzonitrile

Product 1

HCID 183163923-Chloro-4-isothiocyanato-benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of thiophosgene (2 mL) in water (5 mL) was added 4-amino-3-chloro-benzonitrile (1 g, 7 mmol) in small portions over a period of 1 h at 25° C. The mixture was extracted with ethyl acetate (3×25 mL). Combined organic phase was washed with brine (1×50 mL), dried (MgSO4) and concentrated to dryness in vacuo. The title compound 3d was obtained as a tan solid (1.3 g, 96% yield).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×25 mL)
  2. washCombined organic phase was washed with brine (1×50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-90fc7827956e45d5861cd869e18723af
Source dataset
uspto-grants-2014_08
Patent number
US08809550B2

Reaction notes

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