تفاعل #67023

معادلة التفاعل

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

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared by previously published procedures
2. 2
   درجة الحرارةat reflux for 4 hours
3. 3
   أخرىthe charcoal removed by filtration
4. 4
   غسيلThe charcoal was washed several times with ethanol
5. 5
   تركيزthe filtrate then concentrated
6. 6
   workup.ADDITIONWater (200 mL) was added
7. 7
   تركيزconcentrated
8. 8
   أخرىto 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
    أخرىthe organic layer removed
12. 12
    درجة الحرارةThe aqueous layer was cooled to 0° C.
13. 13
    أخرىresulting in the formation of a cloudy oily precipitate
14. 14
    استخلاصThe mixture was extracted with ethyl acetate (3×)
15. 15
    تجفيفthe combined organic extracts dried over sodium sulfate
16. 16
    تركيزconcentrated

الإجراء التجريبي

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%).

المصدر