Lithium Hydroxide → 2,6-Difluoro-4-(5-methyl-3-phenyl-isoxazol-4-yl)benzenesulfonamide

HRID 47655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47655
C(OC[S:6]([C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])=[CH:11][C:10]=1[F:28])(=[O:8])=[O:7])(=O)C.[OH-].[Li+].[NH:31](S(O)(=O)=O)O>C1COCC1.CO.O>[F:28][C:10]1[CH:11]=[C:12]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])[CH:13]=[C:14]([F:15])[C:9]=1[S:6]([NH2:31])(=[O:8])=[O:7]

Komponenten

7

Edukt 3

HCID 3939Lithium Hydroxide2×HCID 170246Hydroxysulfamic acidHCID 22745761{[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl}methyl acetate

Produkt 1

HCID 99682552,6-Difluoro-4-(5-methyl-3-phenyl-isoxazol-4-yl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of {[2,6-difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl}methyl acetate (1.5 g, 3.9 mmol) in THF (25 mL) and methanol (25 mL) was added a solution of lithium hydroxide (0.50 g, 12 mmol) in water (4 mL). The resulting solution was stirred at room temperature for 1 hour. Additional solution of lithium hydroxide (0.60 g, 14 mmol) in water (8 mL) was added, followed by solid hydroxylamine sulfonic acid (1.6 g, 14.1 mmol) and methanol (5 mL). The reaction mixture was stirred overnight and poured into water (250 mL). The 2,6-difluoro-4-(5-methyl-3-phenyl-isoxazol-4-yl)benzenesulfonamide was isolated as a white solid (1.08 g, 85%). MP 226.1-226.2° C. 1H NMR (CD3OD/400 MHz) 7.36-7.46 (m, 5H), 6.95 (d, 2H, J=9.4), 2.51 (s, 3H). ESHRMS m/z 351.0621 (M+H+, Calcd 351.0615). Anal. Calcd for C16H12F2N2O3S: C, 54.85; H, 3.45; N, 8.00. Found: C, 54.95; H, 3.51; N, 7.81.

Aufarbeitung

  1. stirringThe reaction mixture was stirred overnight

Quellen und Nachweise

ORD-Eintrag
ord-ea6589be688c435082ec50d5651785d4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699884B2

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