Methanol → HCID 19023250, compound

HRID 1034285Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[CH3:21]I.CO>C1COCC1>[CH3:21][N:9]([CH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:20][CH:19]=1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (80% dispersion in oil) (0.24 g, 10 mmol) was added to a stirred solution of N-4-methylbenzyl phenylsulphonamide (2.47 g, 10 mmol) in dry THF (50 mi) under argon. After 1.5 h the grey solid of sodium hydride disappeared and a white precipitate formed. The mixture was cooled to 0° C. and treated with methyl iodide (0.62 ml, 10 mmol). The reaction was allowed to warm to ambient temperature and stirred or 16 h. Methanol (1 ml) was added and the reaction mixture evaporated to dryness. The residue was partitioned between ethyl acetate (80 ml) and water (80 ml). The organic layer was separated, washed with water (2×50 ml), dried over MgSO4, filtered and the solvent removed to give the crude product. Flash chromatography (flash silica, gradient elution 0-10% ethyl acetate in hexane) gave, after crystallisation from ethyl acetate/hexane, N-methyl N-4-methylbenzyl phenylsulphonamide (0.89 g, 34%) as a white crystalline solid.

Workup

customa white precipitate formed
temperatureto warm to ambient temperature
customthe reaction mixture evaporated to dryness
customThe residue was partitioned between ethyl acetate (80 ml) and water (80 ml)
customThe organic layer was separated
washwashed with water (2×50 ml)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed

Sources & evidence

ORD record: ord-a3cd8490427349af839ea0f933916d78
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05314880

Reaction notes

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