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

HRID 1838512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838512
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 C,16H12F2N2O3S: 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-65899fcdb3094048aa5491206fc40f06
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673818B2

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