Sodium Bicarbonate → 6,6-Difluoro-5-methyl-5-hexenyl benzo[1,2,5]thiadiazole-5-carboxylate

HRID 917358

반응식

HRID 917358 반응식
CS([O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:14])=[C:11]([F:13])[F:12])(=O)=O.[N:15]1[S:19][N:18]=[C:17]2[CH:20]=[C:21]([C:24](O)=[O:25])[CH:22]=[CH:23][C:16]=12.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[N:15]1[S:19][N:18]=[C:17]2[CH:20]=[C:21]([C:24]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:14])=[C:11]([F:13])[F:12])=[O:25])[CH:22]=[CH:23][C:16]=12

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 6020112,1,3-Benzothiadiazole-5-carboxylic acidHCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonate

생성물 1

HCID 691809276,6-Difluoro-5-methyl-5-hexenyl benzo[1,2,5]thiadiazole-5-carboxylate수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:19)

출처 및 근거

ORD 기록
ord-2677bad272544f568cd6e7a59e95e6c1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273878B2

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