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3-Amino-5-methylisoxazole → 4-acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamide

HRID 347333
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HRID 347333 반응식
[NH2:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.[C:8]([C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=[O:10])[CH3:9]>N1C=CC=CC=1.O>[C:8]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([NH:1][C:2]2[CH:6]=[C:5]([CH3:7])[O:4][N:3]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1)(=[O:10])[CH3:9]
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참가 물질

5

반응물 2

HCID 661723-Amino-5-methylisoxazoleHCID 2664184-Acetylbenzenesulfonyl chloride

생성물 1

HCID 85190264-acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamide수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매2회

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온도
0 °C

실험 절차

Ex-1B: To a solution of 3-amino-5-methylisoxazole (0.27 g, 2.75 mmol) in pyridine (1 mL) at 0° C. was added a solution of 4-acetylbenzenesulfonyl chloride (0.50 g, 2.29 mmol) in 1 mL pyridine dropwise to the reaction. The resulting solution was stirred at 0° C. for 30 min and then warmed to room temperature and stirred for an additional 18 h. The mixture was diluted with water (100 mL), cooled to 0° C., and stirred for 1 h. The resulting precipitate was collected on filter paper and rinsed with several portions of water. The filtrate was acidified with 3 N HCl and the resulting precipitate was collected and rinsed with water. The solids were combined and dried in vacuo to afford 0.50 g (80%) of 4-acetyl-N-(5-methylisoxazole-3-yl)benzenesulfonamide as a pale green solid, mp 189–190° C. 1H-NMR (300 MHz, DMSO-d6) δ 8.14 (d, 2H, J=8.1 Hz), 7.98 (d, 2H, J=8.1 Hz), 6.16 (s, 1H), 2.62 (s, 3H), 2.30 (s, 3H). HRMS (EI) Calcd. for C12H12N2O4S: 280.0518 (M+); Found: 280.0514. Anal. Calcd. for C12H12N2O4S: C, 51.42; H, 4.32; N, 9.99; S, 11.44; Found: C, 51.73; H, 4.39; N, 10.12; S, 11.30.

후처리

  1. customdropwise to the reaction
  2. temperaturewarmed to room temperature
  3. stirringstirred for an additional 18 h
  4. temperaturecooled to 0° C.
  5. stirringstirred for 1 h
  6. customThe resulting precipitate was collected
  7. filtrationon filter paper
  8. washrinsed with several portions of water
  9. customthe resulting precipitate was collected
  10. washrinsed with water
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-cd107af4533444b28520253194c9e41d
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07173129B2

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