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

HRID 34423

反応式

HRID 34423 の反応式
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]

参加物

6

反応物 4

HCID 6654(+-)-alpha-PineneHCID 237411,2-EpoxyhexadecaneHCID 178418558HCID 178418558、化合物HCID 178435042HCID 178435042、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8d01f1ee4dd4295b38fcd5505ac3b4c
出典データセット
uspto-grants-1988_08
特許番号
US04761482

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