Boron trifluoride etherate → 3-[3-(1,3-Dithiolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49009

반응식

HRID 49009 반응식
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=C(C=O)[C:17]=3[CH:23]=2)[C:3]1=[O:24].[CH:25]([SH:28])([SH:27])[CH3:26].B(F)(F)F.[CH3:33][CH2:34]OCC>C(Cl)Cl>[S:27]1[CH2:34][CH2:33][S:28][CH:25]1[C:26]1[C:17]2[CH:23]=[C:13]([N:4]3[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:9])([F:11])[F:10])[N:2]([CH3:1])[C:3]3=[O:24])[CH:14]=[CH:15][C:16]=2[S:20][N:19]=1

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 336451,1-EthanedithiolHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

생성물 1

HCID 206342033-[3-(1,3-Dithiolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil수율 46.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.300 g, 0.850 mmol) and methylene chloride is added ethanedithiol (0.0940 g, 1.00 mmol) and boron trifluoride-etherate (0.200 ml). The resultant mixture is stirred overnight at room temperature and partitioned between methylene chloride and saturated sodium bicarbonate. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to a yellow solid which is stirred in hot methylcyclohexane and filtered to afford the title compound as a light yellow solid (0.170 g, 46.3%, mp 227-232° C.) which is identified by NMR spectral analysis.

후처리

  1. custompartitioned between methylene chloride and saturated sodium bicarbonate
  2. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo to a yellow solid which
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-8bf089df8a384e13a27e826f43e36cc3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706663B2

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