반응 #321594

반응 방정식

Carbonyldiimidazole

piperonylic acid

N-(4-bromo-3-methyl-5-isoxazolyl)-2-aminocarbonylthiophene-3-sulfonamide

N-(4-bromo-3-methyl-5-isoxazolyl)-2-(aminocarbonyl)thiophene-3-sulfonamide

NaH

→

N-(4-bromo-3-methyl-5-isoxazolyl)-2-{[(3,4-methylenedioxy)benzoyl]aminocarbonyl}thiophene-3-sulfonamide

수율 3.6%

용매

Water

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 8 hours
2. 2
   기타to destroy the excess NaH
3. 3
   기타The solvent was then evaporated
4. 4
   기타the residue was partitioned between 1N HCl and EtOAc
5. 5
   건조The organic layer was dried (MgSO4)
6. 6
   여과the solid filtered
7. 7
   농축the filtrate concentrated
8. 8
   기타The residue was recrystalized from EtOAc

실험 절차

Carbonyldiimidazole (21 3 mg. 1.31 mmol) was added to a solution of piperonylic acid (181.5 mg., 1.09 mmol) in dry THF (10 ml). The resulting mixture was stirred for 15 minutes. N-(4-bromo-3-methyl-5-isoxazolyl)-2-aminocarbonylthiophene-3-sulfonamide (Example 89) (400 mg, 1.09 mmol) and NaH (175 mg, 60% in mineral oil, 4.37 mmol) were added sequentially. The mixture was stirred at room temperature for 8 hours. Water was added to destroy the excess NaH. The solvent was then evaporated and the residue was partitioned between 1N HCl and EtOAc. The organic layer was dried (MgSO4), the solid filtered and the filtrate concentrated. The residue was recrystalized from EtOAc to give N-(4-bromo-3-methyl-5-isoxazolyl)-2-{[(3,4-methylenedioxy)benzoyl]aminocarbonyl}thiophene-3-sulfonamide (20 mg, 3.6% yield) as a yellowish powder (m.p. 90°-93° C.).

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