Thionyl Chloride → 4-Isothiocyanatobenzoyl chloride
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
Procedure
A mixture of 500 mg (2.79 mmol) of 4-carboxyphenyl-isothiocyanate 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 6 as an off-white solid.
Workup
- temperaturewas refluxed for 6 hours
- concentrationThe reaction mixture was concentrated at reduced pressure
- customwas pumped at high vacuum overnight
- customThe solid was triturated with a small amount of hexane
- filtrationcollected by suction filtration
Sources & evidence
- ORD record
- ord-21dea30e78a5476fb59b3870119b6586
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476199B1
Reaction notes
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