4-Chlorobenzoyl chloride → 4-Chlorobenzoyl isothiocyanate

HRID 1995899Notes

Reaction equation

HRID 1995899 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]([S-:13])#[N:12].[K+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]=[C:11]=[S:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 2321624-Chlorobenzoyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-chlorobenzoyl chloride (127.1 ml) in 100 ml of dry toluene is added to a vigorously stirred suspension of dried KSCN (106.90 g) in about one liter of dried toluene. The reaction mixture is heated to reflux and after addition is completed the mixture is refluxed overnight. The reaction mixture is allowed to cool, KCl filtered and the filtrate evaporated leaving a reddish residue which solidifies on standing. The residue is vacuum distilled, using a steam filled condenser, yielding 152.4 g of a distillate, b.p. 88°-90° (0.350 torr).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. additionafter addition
  4. temperatureis refluxed overnight
  5. temperatureto cool
  6. filtrationKCl filtered
  7. customthe filtrate evaporated
  8. customleaving a reddish residue which
  9. distillationdistilled
  10. additionfilled condenser
  11. customyielding 152.4 g of a distillate, b.p. 88°-90° (0.350 torr)

Sources & evidence

ORD record
ord-922fc8bfd03b401dbd0212bc552ff896
Source dataset
uspto-grants-1983_09
Patent number
US04406897

Reaction notes

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