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

HRID 1493649노트

반응식

HRID 1493649 반응식
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

참가 물질

3

반응물 1

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

생성물 1

HCID 647455HCID 647455, 화합물수율 47%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  1. customwas dried under vacuum

출처 및 근거

ORD 기록
ord-b99851fafdc143019dcbba743d964cbb
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05023275

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