تفاعل #162715

معادلة التفاعل

sodium hydroxide

(Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate

butyl acetate

trimethylsilyl isothiocyanate

sodium hydroxide

→

desired product

المردود 53.2%

2-(6-(5-Chloro-2-methoxyphenyl)-4-oxo-2-thioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamide

المردود 53.2%

المذيبات

methanol water

ظروف التفاعل

المعالجة

1. 1
   أخرىA reaction vessel equipped with an efficient stirrer
2. 2
   درجة الحرارةthe mixture was heated to reflux
3. 3
   workup.WAITAfter 30 min
4. 4
   أخرىthe organic layer was separated
5. 5
   استخلاصThe combined aqueous phases were extracted twice with dichloromethane (2×45 mL)
6. 6
   ترشيحfiltered
7. 7
   workup.ADDITIONtreated with 6N HCl until a pH of 2.5
8. 8
   أخرىthe resulting solid was isolated by vacuum filtration
9. 9
   درجة الحرارةheated
10. 10
    workup.STIRRINGwith stirring at 50° C. for 2 hours
11. 11
    درجة الحرارةcooled to room temperature
12. 12
    أخرىbefore collecting the solid
13. 13
    ترشيحby vacuum filtration
14. 14
    أخرىpulling dry
15. 15
    أخرىdrying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours

الإجراء التجريبي

A reaction vessel equipped with an efficient stirrer was charged with (Z)-ethyl 3-((2-amino-2-oxoethyl)amino)-3-(5-chloro-2-methoxyphenyl)acrylate (15 g, 50.2 mmol), butyl acetate (150 mL) and trimethylsilyl isothiocyanate (160.7 mmole, 21.1 g, 22.7 mL) and the mixture was heated to reflux. After 15 hours, the mixture was cooled to 30° C. and treated with 1 N aqueous sodium hydroxide (112.5 mL, 112.5 mmoles). After 30 min, the organic layer was separated and extracted with another portion of 1 N sodium hydroxide (37.5 mL, 37.5 mmoles). The combined aqueous phases were extracted twice with dichloromethane (2×45 mL), filtered, and treated with 6N HCl until a pH of 2.5 was achieved. After stirring for 1 hour, the resulting solid was isolated by vacuum filtration, resuspended in 100 mL of a 1:1 methanol-water solution, heated with stirring at 50° C. for 2 hours, and cooled to room temperature before collecting the solid by vacuum filtration, pulling dry and drying in a vacuum oven (20 mm Hg, 50° C.) for 12 hours to afford 8.7 g of the desired product as a tan solid.

المصدر