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

HRID 1886451Notes

Reaction equation

HRID 1886451 reaction equation
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

Participants

3

Reactant 1

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

Product 1

HCID 647455HCID 647455, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. customwas dried under vacuum

Sources & evidence

ORD record
ord-8c6e0f8483d24e799b31c8dfe67baba7
Source dataset
uspto-grants-1992_09
Patent number
US05151447

Reaction notes

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