Methanol → HCID 18617288, compound

HRID 842877Notes

Reaction equation

HRID 842877 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[C:3]=1[Br:8].[H-].[Na+].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>C1COCC1.O>[Br:8][C:3]1[C:4]([CH3:7])=[N:5][O:6][C:2]=1[NH:1][S:17]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:19])=[O:18]

Participants

7

Reactant 4

HCID 887MethanolHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydride2×HCID 104875194-Bromo-3-methylisoxazol-5-amine

Product 1

HCID 18617288HCID 18617288, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 5-amino-4-bromo-3-methylisoxazole (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0° C. After stirring at 0-50° C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0° C. and benzenesulfonyl chloride (0.283 ml, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5° C. Excess sodium hydride was decomposed by the addition of methanol (0.4 ml) followed by water (0.5 ml). The solvent was removed under reduced pressure. The residue was dissolved in water (20 ml), basified to pH 8-9 by the addition of sodium hydroxide and extracted with ethyl acetate (2×10 ml) to remove the neutral impurities. The aqueous layer was acidified with concentrate HCl (pH 2-3) and extracted with ethyl acetate (3×10 ml) The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide. The pure material was obtained by recrystallization using hexanes/ethyl acetate (0.59 g, 93% yield), m.p. 142-144° C.

Workup

  1. temperaturethe reaction was warmed to room temperature for 10 min.
  2. customthe reaction
  3. temperatureThe reaction mixture was re-cooled to 0° C.
  4. stirringStirring
  5. waitwas continued for 20 min. at 0-5° C
  6. customThe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in water (20 ml)
  8. additionbasified to pH 8-9 by the addition of sodium hydroxide
  9. extractionextracted with ethyl acetate (2×10 ml)
  10. customto remove the neutral impurities
  11. extractionextracted with ethyl acetate (3×10 ml) The combined organic layer
  12. dry with materialwas dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a34bb3488f2641fd872667c126554897
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

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