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 49003

반응식

HRID 49003 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 room temperature, stirred for 18 hrs, refluxed for three hrs, 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. temperaturerefluxed for three hrs
  3. temperaturecooled
  4. filtrationfiltered through a pad of diatomaceous earth
  5. concentrationThe resultant filtrate is concentrated in vacuo
  6. customto obtain an aqueous mixture
  7. extractionThe aqueous mixture is extracted with methylene chloride
  8. extractionThe organic extract
  9. washis washed sequentially with water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customto obtain a solid

출처 및 근거

ORD 기록
ord-6b3cd572d4d840a59b547b957ebf8cee
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706663B2

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