반응 #162818

반응 방정식

1,3-diphenyl-pyrimidine-2,4,6-trione

Phosphorus oxychloride

→

6-chloro-1,3-diphenyl-1H-pyrimidine-2,4-dione

수율 74.0%

용매

water

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the completion of the dropwise addition
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   온도under heating at 110° C. for 3 hrs
4. 4
   온도to cool to room temperature
5. 5
   workup.STIRRINGthe mixture was stirred at room temperature
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The organic layer was washed with brine and saturated aqueous sodium hydrogen carbonate
8. 8
   건조dried over anhydrous sodium sulfate. Anhydrous sodium sulfate
9. 9
   여과was filtered off
10. 10
    농축the filtrate was concentrated under reduced pressure
11. 11
    기타The residue was purified by column chromatography (hexane:ethyl acetate=2:1→3:2)

실험 절차

To 1,3-diphenyl-pyrimidine-2,4,6-trione 19 (78.0 g) obtained in Step 1 was added water (16 ml). Phosphorus oxychloride (422 ml) was added dropwise under stirring at room temperature over 50 min. After the completion of the dropwise addition, the mixture was stirred under heating at 110° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was added to ice water by small portions and the mixture was stirred at room temperature and extracted with ethyl acetate. The organic layer was washed with brine and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. Anhydrous sodium sulfate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=2:1→3:2) to give 6-chloro-1,3-diphenyl-1H-pyrimidine-2,4-dione 20 (61.5 g, yield 74%) as pale-yellow crystals.

출처