Benzoyl chloride → Benzoyl isothiocyanate

HRID 1953197Notes

Reaction equation

HRID 1953197 reaction equation
[S-:1][C:2]#[N:3].[NH4+].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CC(C)=O>[C:5]([N:3]=[C:2]=[S:1])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanate

Product 1

HCID 68284Benzoyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ammonium thiocyanate (12.35 g) was dissolved in acetone (AR grade, 120 ml) and benzoylchloride (17.3 ml) was added dropwise with stirring over 2 mins. The temperature rose from 22° C. to 38° C. over the addition and a white precipitate formed. The reaction was stirred at room temperature for a further 75 mins and then filtered, and washed with acetone (20 ml) to give a solution of benzoylisothiocyanate. This was added dropwise with stirring to the amine solution, over 40 mins. The temperature rose from 23° C. to 36° C. during the addition. A thick cream precipitate formed. The reaction was allowed to stir at room temperature for 16 hours and then the product was collected by filtration, washed with water (30 ml), sucked dry and then dried in vacuo at 60° C.

Workup

  1. additionThe temperature rose from 22° C. to 38° C. over the addition
  2. customa white precipitate formed
  3. stirringThe reaction was stirred at room temperature for a further 75 mins
  4. filtrationfiltered
  5. washwashed with acetone (20 ml)

Sources & evidence

ORD record
ord-e9e4f692fd53421d8955d0ab87a6907f
Source dataset
uspto-grants-2000_09
Patent number
US06114578

Reaction notes

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