Water → HCID 18950737, compound

HRID 1492541Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:9][CH:8]=1.[C:33](Cl)(=[O:37])[O:34][CH2:35][CH3:36].O>CN(C)C=O>[CH2:35]([O:34][C:33]([N:15]([CH2:14][CH:13]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][O:4][CH3:3])=[CH:12][CH:11]=1)[CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[O:37])[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

The portion of 120 mg of 60% sodium hydride were suspended in 10 ml of dimethylformamide, and cooled to 0° C., followed by dropwise addition of 1.22 g of N-[2-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide, and then followed by addition of 326 mg of ethyl chlorocarbonate. After stirring at room temperature for 19 hours, the reaction mixture was poured into water. The aqueous phase was extracted with ethyl acetate, and the organic phase was washed in saturated aqueous sodium chloride and dried over magnesium sulfate, to distill off the solvent. The obtained residue was subjected to chromatography on a silica gel column, and from the fraction eluted with methylene chloride was obtained 1.12 g of N-ethoxycarbonyl-N-[2-(4-methoxymethyloxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide.

Workup

extractionThe aqueous phase was extracted with ethyl acetate
washthe organic phase was washed in saturated aqueous sodium chloride
dry with materialdried over magnesium sulfate
distillationto distill off the solvent
washfrom the fraction eluted with methylene chloride

Sources & evidence

ORD record: ord-1dd68c1194d8411e8778dc9576695c7a
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374641

Reaction notes

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