تفاعل #45883

معادلة التفاعل

hydrochloric acid

Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate

trimethylaluminium n-hexane

dimethylamine hydrochloride

→

compound

المردود 83.0%

2-(4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylacetamide

المردود 83.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةby heating
2. 2
   درجة الحرارةunder reflux in an oil bath at 120° C. for 15 hours
3. 3
   workup.ADDITIONwas added to the reaction liquid
4. 4
   استخلاصAfter extraction with ethyl acetate
5. 5
   غسيلthe obtained organic layer was washed with saturated brine
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   أخرىthe insoluble matter was separated by filtration
8. 8
   أخرىthe residue obtained by concentration
9. 9
   أخرىwas purified by preparative TLC (eluent, chloroform

الإجراء التجريبي

At room temperature, trimethylaluminium/n-hexane solution (1.03 mol/l) (547 μl, 0.563 mmol) was added to a toluene (2 ml) suspension of dimethylamine hydrochloride (38.3 mg, 0.469 mmol), followed by stirring at room temperature for 30 minutes. Methyl (4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)acetate (I-295) (65.0 mg, 0.188 mmol) was added to the reaction liquid, followed by heating under reflux in an oil bath at 120° C. for 15 hours. With cooling with ice, 1 N hydrochloric acid was added to the reaction liquid. After extraction with ethyl acetate, the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, then the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (56.0 mg, 83%) as a white solid.

المصدر