Water → ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylate

HRID 1639845

Reaktionsgleichung

Reaktionsgleichung von HRID 1639845
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[S:17]1[C:21]2[C:22]([CH:26]=O)=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1.O>O1CCCC1>[S:17]1[C:21]2[C:22](/[CH:26]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[N:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 14835681Benzo[d][1,2,3]thiadiazole-7-carbaldehyde

Produkt 1

HCID 66720648ethyl(2E)-3-(1,2,3-benzothiadiazol-7-yl)acrylateAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a suspension of 55% sodium hydride (1.81 g, 41.5 mmol) in tetrahydrofuran (30 mL) was added a solution of ethyl diethylphosphonoacetate (8.31 mL, 41.5 mmol) in tetrahydrofuran (10 mL) at 0° C. and the mixture was stirred for 20 min. To the reaction mixture was added a solution of 1,2,3-benzothiadiazole-7-carbaldehyde (6.20 g, 37.8 mmol) in tetrahydrofuran (60 mL) at 0° C. and the mixture was stirred at room temperature for 4 hr. Water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) and recrystallization (ethyl acetate/hexane) to give the title compound (8.70 g, yield 98%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) and recrystallization (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4b0a602c34f14e11b86034dc0869918a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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