反応 #162818

反応方程式

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

Phosphorus oxychloride

→

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

収率 74.0%

溶媒

water

反応条件

後処理

1. 1
   workup.ADDITIONAfter the completion of the dropwise addition
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   温度under heating at 110° C. for 3 hrs
4. 4
   温度to cool to room temperature
5. 5
   workup.STIRRINGthe mixture was stirred at room temperature
6. 6
   抽出extracted with ethyl acetate
7. 7
   洗浄The organic layer was washed with brine and saturated aqueous sodium hydrogen carbonate
8. 8
   乾燥dried over anhydrous sodium sulfate. Anhydrous sodium sulfate
9. 9
   ろ過was filtered off
10. 10
    濃縮the filtrate was concentrated under reduced pressure
11. 11
    その他The residue was purified by column chromatography (hexane:ethyl acetate=2:1→3:2)

実験手順

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.

出典