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

HRID 1838512ノート

反応式

HRID 1838512 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒3 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  1. stirringThe reaction mixture was stirred overnight

出典と根拠

ORDレコード
ord-65899fcdb3094048aa5491206fc40f06
出典データセット
uspto-grants-2004_01
特許番号
US06673818B2

反応ノート

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