Hydrogen Peroxide → 2-(2-Pinanylthio)-5-(octyldithio)-1,3,4-thiadiazole

HRID 34422

Reaction equation

[CH3:1][C:2]1[CH:7]2[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6]2)[CH2:4][CH:3]=1.[SH:11][C:12]1[S:13][C:14]([SH:17])=[N:15][N:16]=1.[CH2:18]([SH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].OO>C(O)(C)C>[CH:7]12[CH2:6][CH:5]([C:8]1([CH3:10])[CH3:9])[CH2:4][CH2:3][C:2]2([S:11][C:12]1[S:13][C:14]([S:17][S:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[N:15][N:16]=1)[CH3:1]

Participants

Conditions

Temperature: 155 °C

Procedure

Alpha-pinene (38 g, 0.28 mol) and 2,5-dimercapto-1,3,4-thiadiazole (40 g, 0.27 mol) were charged to the reaction flask and cautiously heated to 155° C. since the reaction was exothermic. The reaction was maintained at 155° C. for 15 min. and then cooled. Isopropanol (32 g) and n-octylmercaptan (43.7 g, 0.30 mol) were charged. Hydrogen peroxide, 35% (60 g, 0.62 mol) was added slowly while maintaining the temperature at 40°-50° C. The reaction was then allowed to stand overnight. The product was extracted with 150 ml of n-hexane and washed with 150 ml of 1M sodium carbonate. The organic layer was dried over magnesium sulfate, filtered, and the solvent removed by rotary evaporation.

Workup

temperatureThe reaction was maintained at 155° C. for 15 min.
temperaturecooled
temperaturewhile maintaining the temperature at 40°-50° C
extractionThe product was extracted with 150 ml of n-hexane
washwashed with 150 ml of 1M sodium carbonate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
customthe solvent removed by rotary evaporation

Sources & evidence

ORD record: ord-63e6f5db205045cbb08b8a090078ddbd
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04761482

Linked notes

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