반응 #67023

반응 방정식

Charcoal

Sodium hydroxide

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-N-(2-chloro-4-sulfamoylphenyl)acetamide

→

2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid

용매

ethanol

반응 조건

후처리

1. 1
   기타prepared by previously published procedures
2. 2
   온도at reflux for 4 hours
3. 3
   기타the charcoal removed by filtration
4. 4
   세척The charcoal was washed several times with ethanol
5. 5
   농축the filtrate then concentrated
6. 6
   workup.ADDITIONWater (200 mL) was added
7. 7
   농축concentrated
8. 8
   기타to remove all ethanol
9. 9
   workup.ADDITIONWater (200 mL) and ethyl acetate (250 mL) were added
10. 10
    workup.STIRRINGthe mixture stirred vigorously for 15 min
11. 11
    기타the organic layer removed
12. 12
    온도The aqueous layer was cooled to 0° C.
13. 13
    기타resulting in the formation of a cloudy oily precipitate
14. 14
    추출The mixture was extracted with ethyl acetate (3×)
15. 15
    건조the combined organic extracts dried over sodium sulfate
16. 16
    농축concentrated

실험 절차

Sodium hydroxide solution (2M aqueous, 33.7 mL, 67 mmol, 2 eq) was added to a suspension of 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)-N-(2-chloro-4-sulfamoylphenyl)acetamide (prepared by previously published procedures, see US 2009/0197825; 20 g, 34 mmol) in ethanol (200 mL) and the mixture heated at reflux for 4 hours. Charcoal (10 g) was added, the mixture stirred at room temperature for 12 hours and the charcoal removed by filtration. The charcoal was washed several times with ethanol and the filtrate then concentrated. Water (200 mL) was added and then concentrated to approx. one third volume to remove all ethanol. Water (200 mL) and ethyl acetate (250 mL) were added, the mixture stirred vigorously for 15 min and the organic layer removed. The aqueous layer was cooled to 0° C. and acidified by treatment with HCl (1N) resulting in the formation of a cloudy oily precipitate. The mixture was extracted with ethyl acetate (3×) and the combined organic extracts dried over sodium sulfate and concentrated to give 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid as an off white solid (11.2 g, 82%).

출처