海萝胶 → 2,1,3-苯并噻二唑-5-甲酸

HRID 917357

反应方程式

HRID 917357 反应方程式
C(O)C.[N:4]1[S:8][N:7]=[C:6]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=[CH:12][C:5]=12.[OH-].[Na+].Cl>O>[N:4]1[S:8][N:7]=[C:6]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:5]=12

参与物

6

反应物 4

HCID 313海萝胶HCID 702乙醇HCID 14798二甲基对苯二胺二盐酸HCID 696381苯2,1,3-噻重氮-5-羧酸酯

产物 1

HCID 6020112,1,3-苯并噻二唑-5-甲酸收率 94.3%

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

To 30 ml of ethanol was dissolved 2.0 g (10 mmol) of methyl benzo[1,2,5]thiadiazole-5-carboxylate, followed by the addition of 3.3 g of a 25% aqueous solution of sodium hydroxide and stirring at room temperature for 3 hours. To the reaction liquid was added 50 ml of water and a dilute hydrochloric acid to make pH of 2. Crystal precipitated was filtered off and dried under reduced pressure to obtain 1.7 g (yield: 92%) of benzo[1,2, 5]thiadiazole-5-carboxylic acid. In a separate reactor, 0.50 g (2.2 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 0.43 g (2.4 mmol) of benzo[1,2,5]thiadiazole-5-carboxylic acid were dissolved in 7 ml of N,N-dimethylformamide, followed by the addition of 0.37 g (4.4 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:19) to obtain 0.44 g (yield: 64%) of 6,6-difluoro-5-methyl-5-hexenyl benzo[1,2,5]thiadiazole-5-carboxylate.

后处理

  1. customTo the reaction liquid
  2. customCrystal precipitated
  3. filtrationwas filtered off
  4. customdried under reduced pressure

来源与证据

ORD记录
ord-bc7db2e9ed7042a3a38e5ecbf16e02bf
来源数据集
uspto-grants-2007_09
专利号
US07273878B2

关联笔记

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