Dimethylformamide → N-(2,4-Difluoro-3-formylphenyl)-1-propanesulfonamide

HRID 1098383Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH2:13][CH2:14][CH3:15])(=[O:12])=[O:11].C([N-]C(C)C)(C)C.[Li+].C([Li])CCC.C(NC(C)C)(C)C.CN(C)[CH:38]=[O:39]>O1CCCC1.O>[F:1][C:2]1[C:7]([CH:38]=[O:39])=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH2:13][CH2:14][CH3:15])(=[O:12])=[O:11]

Participants

Conditions

Temperature: -78 °C

Procedure

To propane-1-sulfonic acid (2,4-difluoro-phenyl)-amide (72, 1.5 g, 6.38 mmol) in tetrahydrofuran (10 mL) under an atmosphere of nitrogen, cooled in a −78° C. acetone/dry ice bath was added lithium diisopropylamide (0.80 M in tetrahydrofuran, 24 mL, freshly prepared from n-butyllithium and diisopropylamine). After 30 minutes, N,N-dimethyl-formamide (542 μL, 7.018 mmol) was added dropwise to the reaction. The reaction was stirred for 30 minutes at −78° C. and then allowed to warm to room temperature for 40 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% ethyl acetate in hexane to give a light yellow solid (73, 300 mg, 18%). MS (ESI) [M−H+]−=262.3.

Workup

temperatureto warm to room temperature for 40 minutes
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by silica gel column chromatography
washeluting with 5% ethyl acetate in hexane
customto give a light yellow solid (73, 300 mg, 18%)

Sources & evidence

ORD record: ord-02175a80a1cf4990b10a6ad589b9eab8
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143271B2

Reaction notes

Loading…