(+-)-alpha-Pinene → 2-(2-Pinanylthio)-5-(2-hydroxyhexadecylthio)-1,3,4-thiadiazole

HRID 34423

Reaction equation

HRID 34423 reaction equation
SC1SC(S)=NN=1.CC1C2C(C)(C)C(C2)CC=1.[CH:18]12[CH2:26][CH:22]([C:23]1([CH3:25])[CH3:24])[CH2:21][CH2:20][C:19]2([S:28][C:29]1[S:30][C:31]([SH:34])=[N:32][N:33]=1)[CH3:27].[O:35]1[CH:37]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:36]1>C(O)(C)C>[CH:18]12[CH2:26][CH:22]([C:23]1([CH3:24])[CH3:25])[CH2:21][CH2:20][C:19]2([S:28][C:29]1[S:30][C:31]([S:34][CH2:36][CH:37]([OH:35])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])=[N:32][N:33]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6654(+-)-alpha-PineneHCID 237411,2-EpoxyhexadecaneHCID 178418558HCID 178418558, compoundHCID 178435042HCID 178435042, compound

Product 1

HCID 201298502-(2-Pinanylthio)-5-(2-hydroxyhexadecylthio)-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

2,5-Dimercapto-1,3,4-thiadiazole (161.3 g, 1.08 mol) and alphapinene (161.3 g, 1.18 mol) were charged to a reaction vessel and cautiously heated to 120° C. (exothermic reaction). The reaction was maintained at 135° C. for one hour. The intermediate product was stripped under vacuum at 135° C. to remove any unreacted pinene and filtered hot. Methanol (200 ml), hexane (150 ml) and water (15 ml) were charged. The hexane layer was removed and discharded. The methanol layer was stripped of methanol by rotary evaporation and the intermediate product residue was mixed with toluene (200 ml) and then extracted with 1M sodium bicarbonate solution (50 ml). The toluene layer was dried over magnesium sulfate and the solvent removed by rotary evaporation. The yield was 134.1 g (0.468 mol) of the purified intermediate, 2-(2-pinanylthio)-5-mercapto-1,3,4-thiadiazole. This product was reacted with 1,2-epoxyhexadecane (112.3 g, 0.468 mol) by charging both reagents and isopropanol (100 ml) and bringing the reaction to reflux. The solvent was then stripped by rotary evaporation to afford the product.

Workup

  1. custom(exothermic reaction)
  2. temperatureThe reaction was maintained at 135° C. for one hour
  3. customwas stripped under vacuum at 135° C.
  4. customto remove any unreacted pinene
  5. filtrationfiltered hot
  6. additionMethanol (200 ml), hexane (150 ml) and water (15 ml) were charged
  7. customThe hexane layer was removed
  8. customThe methanol layer was stripped of methanol by rotary evaporation
  9. additionthe intermediate product residue was mixed with toluene (200 ml)
  10. extractionextracted with 1M sodium bicarbonate solution (50 ml)
  11. dry with materialThe toluene layer was dried over magnesium sulfate
  12. customthe solvent removed by rotary evaporation
  13. customthe reaction
  14. temperatureto reflux
  15. customThe solvent was then stripped by rotary evaporation
  16. customto afford the product

Sources & evidence

ORD record
ord-e8d01f1ee4dd4295b38fcd5505ac3b4c
Source dataset
uspto-grants-1988_08
Patent number
US04761482

Linked notes

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