Thionyl Chloride → 4-Isothiocyanatobenzoyl chloride

HRID 230079

Reaction equation

HRID 230079 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[S:12])=[CH:6][CH:5]=1)(O)=[O:2].S(Cl)([Cl:15])=O>>[N:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1]([Cl:15])=[O:2])=[CH:5][CH:6]=1)=[C:11]=[S:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2429464-Isothiocyanatobenzoic acid

Product 1

HCID 6376544-Isothiocyanatobenzoyl chlorideYield 93%

Procedure

A mixture of 500 mg (2.79 mmol) of 4-carboxyphenylisothiocyanate and 5 ml of thionyl chloride was refluxed for 6 hours. The reaction mixture was concentrated at reduced pressure and the resulting tan solid was pumped at high vacuum overnight. The solid was triturated with a small amount of hexane and collected by suction filtration to yield 516 mg (93%) of product as an off-white solid.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. customwas pumped at high vacuum overnight
  4. customThe solid was triturated with a small amount of hexane
  5. filtrationcollected by suction filtration

Sources & evidence

ORD record
ord-57092f1f27ce496cbeeb2375c53ed4c5
Source dataset
uspto-grants-2009_07
Patent number
US07566549B2

Linked notes

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