二氯甲烷 → 3-[3-(1,3-Dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49005

反应方程式

HRID 49005 反应方程式
BrC(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.ClCCl.[CH3:29][O:30][CH2:31][O:32][CH3:33]>FC(F)(F)S([O-])(=O)=O.[Ag+].C(O)CO>[O:30]1[CH2:29][CH2:33][O:32][CH:31]1[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1

参与物

6

反应物 3

HCID 6344二氯甲烷HCID 8020甲缩醛HCID 221198393-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

产物 1

HCID 206342023-[3-(1,3-Dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil收率 17.5%

试剂、催化剂与溶剂 2

HCID 76223三氟甲烷磺酸银催化剂4 次HCID 1742,2’-[(1-甲基亚乙基)二(4,1-亚苯基氧亚甲基)]二环氧乙烷与α-氢-ω-羟基聚(氧-1,2-亚乙基)的聚合物溶剂3 次

实验过程

A mixture of 3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.500 g, 10.0 mmol), silver trifluoromethanesulfonate (0.500 g, 19.5 mmol), ethylene glycol (5.00 ml), dichloromethane and dimethoxymethane is stirred three days at room temperature and treated with additional silver trifluoromethanesulfonate (0.300 g, 11.7 mmol). The resultant mixture is stirred one day at room temperature and treated with additional silver trifluoromethanesulfonate (0.400 g, 15.6 mmol) and ethylene glycol (1.00 ml), stirred another day at room temperature and treated again with silver trifluoromethanesulfonate (0.300 g, 11.7 mmol) and ethylene glycol (1.0 ml). After stirring an additional day the mixture is filtered. The filtrate is diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is triturated with hexanes-ethyl acetate to afford the title compound as a white solid (0.070 g, 17.5%, mp 213-216° C.) which is identified by NMR spectral analysis.

后处理

  1. stirringstirred another day at room temperature
  2. stirringAfter stirring an additional day the mixture
  3. filtrationis filtered
  4. additionThe filtrate is diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated with hexanes-ethyl acetate

来源与证据

ORD记录
ord-16b4da2259f54c529f075d0511a069de
来源数据集
uspto-grants-2004_03
专利号
US06706663B2

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