반응 #1571704

반응 방정식

triphosgene

4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline

Intermediate 11

4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline

DCM

Triethylamine

acetohydrazide

→

title compound

수율 82.1%

5-methyl-4-(4-{[4-methyl-3-(methyloxy)phenyl]oxy}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

수율 82.1%

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature overnight
2. 2
   농축The solvent was concentrated in vacuum
3. 3
   workup.DISSOLUTIONthe residue was dissolved in a 2M aqueous solution of NaOH (15 mL)
4. 4
   온도the mixture was heated
5. 5
   온도to reflux for 12 h
6. 6
   추출extracted with DCM (3×50 mL)
7. 7
   건조The combined organic phases were dried over Na2SO4
8. 8
   농축concentrated under reduced pressure
9. 9
   기타to give the crude product which
10. 10
    기타was purified by flash chromatography on silica gel

실험 절차

To a solution of 4-{[4-methyl-3-(methyloxy)phenyl]oxy}aniline (Intermediate 11, 336 mg, 1.467 mmol) in DCM (50 mL) Triethylamine (296 mg, 2.93 mmol) was added followed by triphosgene (174 mg, 0.587 mmol). The reaction mixture was stirred at room temperature for 0.5 h. Triethylamine (296 mg, 2.93 mmol) and acetohydrazide (130 mg, 1.76 mmol) were then added and the reaction mixture was stirred at room temperature overnight. The solvent was concentrated in vacuum and the residue was dissolved in a 2M aqueous solution of NaOH (15 mL) and the mixture was heated to reflux for 12 h. The reaction mixture was neutralized with aqueous 6M HCl to pH=7 and extracted with DCM (3×50 mL). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by flash chromatography on silica gel using dichloromethane/methanol as eluents from 100/1 to 50/1 to yield 150 mg of the title compound.

출처