Benzyl Chloride → 2-Benzylthio-2-thiazoline

HRID 2241019

Reaktionsgleichung

Reaktionsgleichung von HRID 2241019
[H-].[Na+].[SH:3][C:4]1[S:5][CH2:6][CH2:7][N:8]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O1CCCC1>[CH2:9]([S:3][C:4]1[S:5][CH2:6][CH2:7][N:8]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178527880HCID 178527880, Verbindung

Produkt 1

HCID 2756772-Benzylthio-2-thiazolineAusbeute 258,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a dry, nitrogen (N2)-purged 500 milliliter (mL) round bottom flask was added 1.15 grams (g) (4.8 mmol) sodium hydride. To this was added 150 mL dry tetrahydrofuran and 5.70 g (4.8 mmol) 2-mercaptothiazoline in 24 mL tetrahydrofuran. After approximately 15 minutes of stirring at room temperature, 5.5 mL (4.8 mmol) benzyl chloride was added and stirred for an additional 5 minutes. Tetrahydrofuran was removed by rotary evaporation and product was dissolved in hexane. After filtration, the product was recrystallized from hexane to yield 2.6 g of white crystals (26% yield). 1H NMR (CDCl3): 3.434 ppm, t, 2H; 4.259 ppm, t, 2H; 4.413 ppm, s, 2H; 7.317 ppm, m, 5H.

Aufarbeitung

  1. stirringstirred for an additional 5 minutes
  2. customTetrahydrofuran was removed by rotary evaporation and product
  3. dissolutionwas dissolved in hexane
  4. filtrationAfter filtration
  5. customthe product was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-e26ac105580344a7b6a2511150fd1477
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723440B2

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