Ammonia → Tert-butyl 3-sulfamoylbenzoate

HRID 252218

Reaktionsgleichung

S(=O)(=O)(O)O.[O-]S([O-])(=O)=O.[Mg+2].Cl[S:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20])(=[O:15])=[O:14].[CH3:25][C:26](O)([CH3:28])[CH3:27].[NH3:30]>C(Cl)Cl.CO>[C:26]([O:21][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([S:13](=[O:15])(=[O:14])[NH2:30])[CH:17]=1)([CH3:28])([CH3:27])[CH3:25]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Sulfuric acid (conc., 498 μL, 9.06 mmol) was added to a suspension of MgSO4 (4.36 g, 36.22 mmol) in CH2Cl2 (36 mL). The reaction mixture was stirred for 15 minutes, treated with 3-chlorosulfonyl-benzoic acid (Aldrich, 2 g, 9.06 mmol) and 2-methyl-propan-2-ol (anhydrous, 4.33 mL, 45.27 mmol), capped tightly, and stirred overnight at room temperature. The next day, the mixture was cooled to 0° C., treated with 7N NH3 in methanol (Aldrich, 40 mL) dropwise, and stirred for 30 minutes. The solvents were removed in vacuo and the crude was dissolved in ethyl acetate and saturated NaHCO3. The organic layer was washed with saturated NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as a white solid (1 g, 42.9% yield). 1H-NMR (CDCl3): δ 8.51-8.53 (m, 1H), 8.20-8.21 (m, 1H), 8.08-8.11 (m, 1H), 7.57-7.62 (m, 1H), 5.09 (bs, 2H), and 1.61 (s, 9H).

Aufarbeitung

customcapped tightly
stirringstirred overnight at room temperature
stirringstirred for 30 minutes
customThe solvents were removed in vacuo
dissolutionthe crude was dissolved in ethyl acetate
washThe organic layer was washed with saturated NaHCO3, water, and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-5cf8e981a9a04de19c96d38c95f3a4b8
Quelldatensatz: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07868023B2

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