Water → N-ethyl-N-(5-fluoro-2-nitrophenyl)methanesulfonamide

HRID 1064491Notes

Reaction equation

[CH2:1]([NH:3][S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2].[H-].[Na+].F[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].O>CN(C=O)C>[CH2:1]([N:3]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19])[S:4]([CH3:7])(=[O:6])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 55 °C

Procedure

N-ethyl-methanesulfonamide (Mijs et al. J. Chem. Soc. Chem. Com. 1972 p412) (5 g 40.6 mmol) was added to a suspension of sodium hydride (1.9 g, 55% in mineral oil) in anhydrous DMF (100 mL) under nitrogen. The mixture was warmed to 55° C. for one hour and 2,4-difluoronitrobenzene (4.4 mL) was added dropwise. The reaction was stirred at 60° C. overnight, poured into water (500 mL) and the product extracted into CH2Cl2 (5×100 mL). The organic extracts were washed with water, dried over MgSO4 and evaporated to give an oily product. The remaining DMF was removed by trituration with petrol. The crude product was purified by flash chromatography (ethyl acetate:petrol 1:1) to yield the desired product which was recrystallised from ethanol. Yield 3.5 g (33%). Calculated N, % 10.68; C, % 41.22; S, % 12.23; H, % 4.23. Found N, % 10.68; C, % 41.39; S, % 12.22; H, % 4.17.

Workup

extractionthe product extracted into CH2Cl2 (5×100 mL)
washThe organic extracts were washed with water
dry with materialdried over MgSO4
customevaporated
customto give an oily product
customThe remaining DMF was removed by trituration with petrol
customThe crude product was purified by flash chromatography (ethyl acetate:petrol 1:1)

Sources & evidence

ORD record: ord-ffe290f2cf4848bebfcef6d8f4cecd27
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969710B2

Reaction notes

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