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

HRID 47655노트

반응식

HRID 47655 반응식
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]

참가 물질

7

반응물 3

HCID 3939Lithium Hydroxide2회HCID 170246Hydroxysulfamic acidHCID 22745761{[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl}methyl acetate

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 962Water용매3회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. stirringThe reaction mixture was stirred overnight

출처 및 근거

ORD 기록
ord-ea6589be688c435082ec50d5651785d4
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699884B2

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