반응 #931702

반응 방정식

dihexylamine

1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid

triethylamine

ethyl chlorocarbonate

→

N,N-dihexyl-1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxamide

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도after cooling to —40° C.
2. 2
   workup.STIRRINGAfter stirring at −40° C. for an hour
3. 3
   온도the temperature was raised to room temperature over an hour
4. 4
   workup.STIRRINGby stirring at room temperature overnight
5. 5
   농축The reaction mixture was concentrated under reduced pressure
6. 6
   workup.ADDITIONthe residue, after addition of ethyl acetate
7. 7
   세척was washed with water, 1N hydrochloric acid
8. 8
   건조a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
9. 9
   기타After removal of the drying agent
10. 10
    여과by filtration
11. 11
    농축the filtrate was concentrated under reduced pressure
12. 12
    기타The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; chloroform)
13. 13
    기타recrystallized from hexane

실험 절차

In 30 ml of tetrahydrofuran were dissolved 0.50 g of 1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxylic acid and 0.87 ml of triethylamine, and after cooling to —40° C., 0.19 ml of ethyl chlorocarbonate was added dropwise over 5 minutes. After stirring at −40° C. for 10 minutes, 0.46 ml of dihexylamine was added dropwise over 5 minutes. After stirring at −40° C. for an hour, the temperature was raised to room temperature over an hour, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue, after addition of ethyl acetate, was washed with water, 1N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel; Wakogel C200 (manufactured by Wako Pure Chemicals), developing solvent; chloroform) and recrystallized from hexane to give 0.53 g of N,N-dihexyl-1-benzyl-1,2-dihydro-2-oxoquinoxaline-3-carboxamide.

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