Dimethylformamide → 5-Cyano-2-methoxybenzene-1-sulfonyl chloride

HRID 733354Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([Cl:13])(=[O:12])=[O:11])[CH:9]=1)(=O)[NH2:2].S(Cl)(Cl)=O.CN(C)C=O>C(OCC)(=O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([Cl:13])(=[O:12])=[O:11])[CH:9]=1)#[N:2]

Participants

Conditions

Temperature: 55 °C

Procedure

5-Carbamoyl-2-methoxybenzenesulfonyl chloride (150 g) was suspended in 1800 mL of ethyl acetate. After 219 mL of thionyl chloride was dropped to the stirred suspension under ice-cooling, 2.3 mL of N,N-dimethylformamide was added to the mixture. After being stirred at 55° C. for 3 hours, the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and water, and the separated organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained crude product was recrystallized from ethyl acetate-hexane to give 86.8 g of 5-cyano-2-methoxybenzenesulfonyl chloride.

Workup

temperaturecooling
concentrationthe reaction mixture was concentrated under reduced pressure
additionTo the residue were added ethyl acetate and water
washthe separated organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customthe obtained crude product
customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-ba1059a36a21458789ab64afc9680997
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589126B2

Reaction notes

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