Water → Methyl 3-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoate

HRID 401767

Reaktionsgleichung

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:6]=1[CH2:7][NH:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.Cl[S:21]([C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])(=[O:23])=[O:22].O>C1COCC1>[CH3:3][O:4][C:5]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:6]=1[CH2:7][N:8]([C:9]1[S:10][CH:11]=[CH:12][N:13]=1)[S:21]([C:24]1[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])(=[O:23])=[O:22]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 239 mg, 5.99 mmol, 1.5 eq) was added portionwise to a solution of N-(2,4-dimethoxybenzyl)-1,3-thiazol-2-amine (Preparation 6, 1 g, 3.995 mmol, 1 eq) in THF (10 ml) at 0° C. The mixture was stirred for 40 minutes before the addition of methyl 3-(chlorosulfonyl)benzoate (937, 3.995 mmol, 1 eq) and the reaction mixture stirred for a further 1 hour at 0° C. and 5 hours at room temperature. Water (2 ml) was added and the THF evaporated in vacuo. The residue was extracted from water (10 ml) into ethyl acetate (3×5 ml), washed with brine, dried over magnesium sulphate, filtered and evaporated in vacuo to yield methyl 3-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}benzoate.

Aufarbeitung

customthe THF evaporated in vacuo
extractionThe residue was extracted from water (10 ml) into ethyl acetate (3×5 ml)
washwashed with brine
dry with materialdried over magnesium sulphate
filtrationfiltered
customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-147ab32cdcac4bc3b5c1e7c9fdc1a636
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08741934B2

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