3(2H)-Isothiazolone, 2-(phenylmethyl)-, hydrochloride (1:1) → HCID 647455、化合物

HRID 1493649ノート

反応式

HRID 1493649 の反応式
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

参加物

3

反応物 1

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

生成物 1

HCID 647455HCID 647455、化合物収率 47%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  1. customwas dried under vacuum

出典と根拠

ORDレコード
ord-b99851fafdc143019dcbba743d964cbb
出典データセット
uspto-grants-1991_06
特許番号
US05023275

反応ノート

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