3(2H)-Isothiazolone, 2-(phenylmethyl)-, hydrochloride (1:1) → HCID 647455, Verbindung

HRID 1493649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1493649
Cl.[CH2:2]([N:9]1[C:13](=[O:14])[CH:12]=[CH:11][S:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O>[CH2:2]([N:9]1[C:13](=[O:14])[CH:12]=[CH:11][S:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

3

Edukt 1

HCID 130137703(2H)-Isothiazolone, 2-(phenylmethyl)-, hydrochloride (1:1)

Produkt 1

HCID 647455HCID 647455, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 58.2 g (0.15 mol) of N,N'-bis-benzyl-3,3'-dithiodipropionamide in 500 ml of ethylene dichloride at 10-15° C. was added dropwise 63.6 g (0.473 mol) of sulfuryl chloride. A clear, light amber solution resulted. After stirring overnight, the solution was concentrated to give about one half volume. Cream-colored solid separated and was collected by filtration, yielding 36.1 g of 2-benzyl-4-isothiazolin-3-one hydrochloride salt; 1.5 g of additional solid separated in the filtrate but proved to be starting material. The filtrate was further evaporated to a brown oil. The oil was redissolved in benzene, treated with decolorizing carbon, and evaporated once again. The resulting light amber oil solidified on standing. This light tan solid was recrystallized from heptane giving 8.0 g(12% yield) of white crystals of 2-benzyl-5-chloro-4-isothiazolin-3-one hydrochloride salt whose m.p. was 58°-59° C. The hydrochloride of the unchlorinated benzyl compound was converted to free base by trituration with water and was dried under vacuum to give 27.0 g (47% yield) of the 2-benzyl-4-isothiazolin-3-one intermediate, m.p.=78°-80° C.

Aufarbeitung

  1. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b99851fafdc143019dcbba743d964cbb
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05023275

Notizen zur Reaktion

Wird geladen…