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

HRID 347333Notes

Reaction equation

HRID 347333 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cd107af4533444b28520253194c9e41d
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

Loading…