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

HRID 917358

Reaktionsgleichung

Reaktionsgleichung von HRID 917358
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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2677bad272544f568cd6e7a59e95e6c1
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273878B2

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