1,4-Dioxane--water (1/1) → 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

HRID 1274577

반응식

HRID 1274577 반응식
Br[CH:2](Br)[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[O:26]1CCOCC1.O>[N+]([O-])([O-])=O.[Ag+].C(Cl)Cl>[CH3:23][N:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][C:17](=[O:18])[N:12]([C:9]2[CH:10]=[CH:11][C:6]3[S:5][N:4]=[C:3]([CH:2]=[O:26])[C:7]=3[CH:8]=2)[C:13]1=[O:24]

참가 물질

5

반응물 2

HCID 218864351,4-Dioxane--water (1/1)HCID 221198393-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

생성물 1

HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.500 g, 0.00100 mol) in a dioxane/water mixture (5:2) is treated with silver nitrate (0.340 g, 0.00200 mol), refluxed for 90 minutes, cooled to and stirred at room temperature overnight, refluxed for three hours, cooled, and filtered through a pad of diatomaceous earth. The resultant filtrate is concentrated in vacuo to obtain an aqueous mixture. The aqueous mixture is extracted with methylene chloride. The organic extract is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel and methylene chloride gives the title product as a solid (0.240 g, mp 193-194.5° C.).

후처리

  1. temperaturerefluxed for 90 minutes
  2. temperaturecooled to and
  3. temperaturerefluxed for three hours
  4. temperaturecooled
  5. filtrationfiltered through a pad of diatomaceous earth
  6. concentrationThe resultant filtrate is concentrated in vacuo
  7. customto obtain an aqueous mixture
  8. extractionThe aqueous mixture is extracted with methylene chloride
  9. extractionThe organic extract
  10. washis washed sequentially with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customto obtain a solid

출처 및 근거

ORD 기록
ord-4b67f8831c904cb99a05607e2293c704
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156700

연결된 노트

불러오는 중…