Water → 5-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

HRID 624586ノート

反応式

HRID 624586 の反応式
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([CH3:10])[C:3]1=[O:11].ClC1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>[Cl-].[Zn+2].[Cl-].CCOC(C)=O>[C:19]([C:6]1[C:5](=[O:9])[N:4]([CH3:10])[C:3](=[O:11])[N:2]([CH3:1])[C:7]=1[CH3:8])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 7964ChlorobenzeneHCID 260751,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione

生成物 1

HCID 8023085-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

1,3,6-Trimethylpyrimidine-2,4(1H,3H)-dione (step 1) (5 g, 32.4 mmol) and chlorobenzene (50 mL) were charged to a 3 necked flask, and the vessel evacuated with nitrogen. Benzoyl chloride (commercial) (11.2 mL, 97 mmol) was added followed by zinc (II) chloride (5 g, 36.7 mmol) in one portion and the reaction was heated to 110° C. for 16 h. The reaction was cooled to RT then poured into water (100 mL) and EtOAc (100 mL). The layers were separated and the aqueous extracted with EtOAc (2×150 mL). The combined organics were washed with water (100 mL) and dried (Na2SO4), filtered under reduced pressure and evaporated to leave an orange solid. The solid was washed with hexane followed by hot diethyl ether, affording the product as an off white solid. The mother liquors were further purified by chromatography on silica, eluting with 10%-100% EtOAc/hexane. The title product was obtained as a pale orange solid.

後処理

  1. customthe vessel evacuated with nitrogen
  2. temperatureThe reaction was cooled to RT
  3. customThe layers were separated
  4. extractionthe aqueous extracted with EtOAc (2×150 mL)
  5. washThe combined organics were washed with water (100 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered under reduced pressure
  8. customevaporated
  9. customto leave an orange solid
  10. washThe solid was washed with hexane
  11. customaffording the product as an off white solid
  12. customThe mother liquors were further purified by chromatography on silica
  13. washeluting with 10%-100% EtOAc/hexane

出典と根拠

ORDレコード
ord-9f1bcb5dcddc4d56af2ac370762ad325
出典データセット
uspto-grants-2016_04
特許番号
US09303035B2

反応ノート

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