Reaktion #45883

Reaktionsgleichung

hydrochloric acid

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

trimethylaluminium n-hexane

dimethylamine hydrochloride

→

compound

Ausbeute 83.0%

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

Ausbeute 83.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby heating
2. 2
   Temperaturunder reflux in an oil bath at 120° C. for 15 hours
3. 3
   workup.ADDITIONwas added to the reaction liquid
4. 4
   ExtraktionAfter extraction with ethyl acetate
5. 5
   Waschenthe obtained organic layer was washed with saturated brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   Sonstigethe insoluble matter was separated by filtration
8. 8
   Sonstigethe residue obtained by concentration
9. 9
   Sonstigewas purified by preparative TLC (eluent, chloroform

Vorschrift

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.

Quelle