Water → 2-(2-Pinanylthio)-5-(t-butylthio)-1,3,4-thiadiazole

HRID 34424

Reaction equation

HRID 34424 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)([CH3:21])([CH3:20])[CH3:19].O>S(=O)(=O)(O)O.C1(C)C(C)=CC=CC=1>[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][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:5][N:6]=1)[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 6654(+-)-alpha-PineneHCID 178418558HCID 178418558, compound

Product 1

HCID 201298522-(2-Pinanylthio)-5-(t-butylthio)-1,3,4-thiadiazole

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7237O-XyleneSolvent2×

Conditions

Temperature
140 °C

Procedure

2,5-Dimercapto-1,3,4-thiadiazole (35 g, 0.23 mol) and alpha-pinene (35 g, 0.26 mol) were charged to a reaction vessel and heated cautiously to 140° C. (exothermic reaction). The reaction was maintained at 135°-155° C. for 15 min. The reaction was fitted with a Dean Stark trap filled with xylene. Xylene (15 ml) was charged to the reaction. The reaction was fitted with an addition funnel containing t-butanol (25 g, 0.34 mol). The alcohol was added slowly with the reaction refluxing. Sulfuric acid (3 drops) was added to accelerate the water removal. The reaction product was isolated after approximately 5 ml (about 0.25 mol) of water were collected. Solvent was stripped by rotary evaporation. The product was mixed with calcium hydroxide (1 g), hexane (about 100 ml), and sufficient acetone (about 50 ml) to maintain one liquid layer. The product was filtered using a filter aid and the solvent removed by rotary evaporation. This afforded the final product.

Workup

  1. custom(exothermic reaction)
  2. temperatureThe reaction was maintained at 135°-155° C. for 15 min
  3. customThe reaction was fitted with a Dean Stark trap
  4. customThe reaction was fitted with an addition funnel
  5. temperaturerefluxing
  6. customthe water removal
  7. customwere collected
  8. customSolvent was stripped by rotary evaporation
  9. additionThe product was mixed with calcium hydroxide (1 g), hexane (about 100 ml), and sufficient acetone (about 50 ml)
  10. temperatureto maintain one liquid layer
  11. filtrationThe product was filtered
  12. customthe solvent removed by rotary evaporation

Sources & evidence

ORD record
ord-ba1ce414a207408996063908143efced
Source dataset
uspto-grants-1988_08
Patent number
US04761482

Linked notes

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