Thionyl Chloride → 3-(N-allylsulfamoyl)benzoyl isothiocyanate

HRID 518758Notes

Reaction equation

[CH2:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12])(=[O:7])=[O:6])[CH:2]=[CH2:3].S(Cl)(Cl)=O.[N-:21]=[C:22]=[S:23].[K+]>ClCCCl>[CH2:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([N:21]=[C:22]=[S:23])=[O:12])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 3-(N-allylsulfamoyl)benzoic acid (2 g, 8.29 mmol) in 1,2-dichloroethane (25 mL) was added thionyl chloride (1.271 mL, 17.41 mmol) dropwise. The suspension was stirred for 2 hours at 80° C. After 2 hours, the reaction mixture was concentrated to an off-white solid. The solid was redissolved in 25 mL acetone, and potassium isothiocyanate (0.967 g, 9.95 mmol) was added. A precipitate formed immediately upon addition. The reaction was stirred at 50° C. After 2 hours, the reaction was filtered, concentrated, and adsorbed onto a silca-gel pre column. The residue was purified by column chromatography, eluting with 20-100% EtOAc in hexanes, to provide 3-(N-allylsulfamoyl)benzoyl isothiocyanate as an off-white solid (0.71 g, 30.3% yield). MS, m/z (C11H10N2O3S2): calcd, 282.0. found, 282.9 [M+H].

Workup

waitAfter 2 hours
concentrationthe reaction mixture was concentrated to an off-white solid
dissolutionThe solid was redissolved in 25 mL acetone
customA precipitate formed immediately upon addition
stirringThe reaction was stirred at 50° C
waitAfter 2 hours
filtrationthe reaction was filtered
concentrationconcentrated
customThe residue was purified by column chromatography
washeluting with 20-100% EtOAc in hexanes

Sources & evidence

ORD record: ord-41dbcc4d7ae84c169c6f90dfa17d4961
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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