Ethanol → 4-fluoro-N-methylbenzene-1-sulfonamide

HRID 2077554Notes

Reaction equation

HRID 2077554 reaction equation
[CH3:1][NH2:2].C(O)C.[F:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>>[F:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:2][CH3:1])(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 6329MethylamineHCID 95884-Fluorobenzenesulfonyl chloride

Product 1

HCID 24400544-fluoro-N-methylbenzene-1-sulfonamide

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with methylamine solution 40% (0.88 ml, 26 mmol) in ethanol (10 ml, 171 mmol). The mixture was chilled to 0° C. in an ice bath, with stirring under inert atmosphere. Then 4-fluorobenzenesulfonyl chloride (1.00 g, 5.1 mmol) was added into the mixture. The resulting mixture was allowed to stir at 0° C., while under inert atmosphere for 30 minutes. The progress of the reaction was monitored by LC/MS, which showed mostly desired product peak. The mixture was diluted with DCM and saturated sodium bicarbonate solution, then extracted the organic layer with DCM (3×25 ml). The organics were combined, dried over sodium sulfate, filtered and concentrated in vacuo. This gave 4-fluoro-N-methylbenzenesulfonamide (0.918 g, 94% yield) as an off-white crystalline solid. MS (ESI pos. ion) m/z: 190 (MH+). Calc'd exact mass for C7H8FNO2S: 189. 1H NMR (400 MHz, chloroform-d): 2.64-2.71 (m, 3H), 4.63 (s, 1H), 7.18-7.28 (m, 2H), 7.88-7.93 (m, 2H).

Workup

  1. stirringto stir at 0° C., while under inert atmosphere for 30 minutes

Sources & evidence

ORD record
ord-0af3f6edbe794920b007f400bbfe8ecd
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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