Phenethyl bromide → 3-(2-phenylethyl)-1,3-benzothiazol-2(3H)-one

HRID 1941156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941156
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].[H][H].[C:15]1([CH2:21][CH2:22]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C)C=O>[CH2:22]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][C:2]1=[O:10])[CH2:21][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

7

Edukt 5

HCID 7666Phenethyl bromideHCID 13625BenzothiazoloneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10931463-(2-phenylethyl)-1,3-benzothiazol-2(3H)-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(1aB) Benzothiazolin-2-one (5.15 g, 34.1 mmol) was dissolved in dimethylformamide (100 ml) and to the solution was added 60% sodium hydride (1.36 g, 34.1 mmol) which was stirred at room temperature until generation of hydrogen gas stopped. Then β-phenylethylbromide (4.89 ml, 35.8 mmol) was added to the solution which was stirred at room temperature for 17 hours. To the reaction solution was added a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed in turn with a saturated sodium bicarbonate solution and saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The crude product thus obtained was purified by subjecting it to silica gel column chromatography to give 6.49 g of 3-phenethylbenzothiazoline-2-one as a white amorphous powder form n-hexane/ethyl (4:1)-eluted fraction (yield: 80%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed in turn with a saturated sodium bicarbonate solution and saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe crude product thus obtained
  6. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-4180b3f6fe5f4fb1956ba874b2beb221
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05703071

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