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

HRID 345183Notes

Reaction equation

HRID 345183 reaction equation
[SH:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[CH3:8][C:9]1[CH:14]2[C:15]([CH3:17])([CH3:16])[CH:12]([CH2:13]2)[CH2:11][CH:10]=1.[C:18]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:28])/[CH:19]=[CH:20]\[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22].C(=O)([O-])[O-].[Na+].[Na+]>>[CH:14]12[CH2:13][CH:12]([C:15]1([CH3:17])[CH3:16])[CH2:11][CH2:10][C:9]2([S:1][C:2]1[S:3][C:4]([S:7][CH:19]([C:18]([O:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[N:5][N:6]=1)[CH3:8]

Participants

5

Reactant 4

HCID 6654(+-)-alpha-PineneHCID 10340Sodium CarbonateHCID 5271569Dibutyl maleateHCID 178418558HCID 178418558, compound

Product 1

HCID 538246702-(2-Pinanylthio)-5-(1,2-dibutoxycarbonylethylthio)-1,3,4-thiadiazole

Conditions

Temperature
100 °C

Procedure

2,5-Dimercapto-1,3,4-thiadiazole (35.0 g, 0.23 mol) was charged into a reaction flask along with alpha-pinene (33.85 g, 0.24 mol). The reaction was heated to 100° C. for 1 hour and then cautiously heated to 120° C. The reaction exothermed and was maintained at 155° C. for 20 min. Dibutyl maleate (53.5 g, 0.55 mol) was added and the reaction was maintained at 155° C. for 3 hours. The reaction product was then cooled, charged with sodium carbonate (about 1 g) and stirred. The product was filtered using a filter aid.

Workup

  1. temperaturecautiously heated to 120° C
  2. customThe reaction exothermed
  3. temperaturewas maintained at 155° C. for 20 min
  4. temperaturethe reaction was maintained at 155° C. for 3 hours
  5. temperatureThe reaction product was then cooled
  6. filtrationThe product was filtered

Sources & evidence

ORD record
ord-e025f922e0aa4e85926140047abbc1f6
Source dataset
uspto-grants-1991_10
Patent number
US05055584

Reaction notes

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