Hexane → HCID 9818054, compound

HRID 429770Notes

Reaction equation

HRID 429770 reaction equation
O[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][CH2:13][NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[OH-].[K+].CN(C)C(Cl)=[S:28].CCCCCC>O.O1CCCC1>[SH:28][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[CH2:12][CH2:13][NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 27871Dimethylthiocarbamoyl chlorideHCID 15410537HCID 15410537, compound

Product 1

HCID 9818054HCID 9818054, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The product obtained in Step A (9 mmol) is added, with stirring, to a solution of potassium hydroxide (10 mmol) dissolved in 15 ml of water and 16 ml of tetrahydrofuran. The solution is cooled using a bath of ice and salt, and dimethylthiocarbamoyl chloride (9 mmol) dissolved in tetrahydrofuran (15 ml) is added dropwise with stirring. After stirring for half an hour while maintaining the cold temperature, the reaction mixture is extracted with chloroform. The organic phases are combined, dried over magnesium sulphate, filtered and then concentrated under reduced pressure. The residue is taken up in diphenyl ether (10 ml) and refluxed for one hour under a nitrogen atmosphere. The diphenyl ether is removed by evaporation under reduced pressure until a solution of about 2 ml has been obtained. The 2 ml of distillate, which are still hot, are poured carefully into 50 ml of hexane to yield, after cooling, a solid which is isolated by filtration. The solid collected in that manner is added to a solution of potassium hydroxide (380 mg) dissolved in a water/methanol mixture (1 ml/10 ml). The solution is refluxed for 12 hours and then cooled and concentrated under reduced pressure. The residue is taken up in 20 ml of chloroform and extracted 3 times with water. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is chromatographed over silica gel to yield the title product.

Workup

  1. temperatureThe solution is cooled
  2. additionis added dropwise
  3. stirringAfter stirring for half an hour
  4. temperaturewhile maintaining the cold temperature
  5. extractionthe reaction mixture is extracted with chloroform
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. temperaturerefluxed for one hour under a nitrogen atmosphere
  10. customThe diphenyl ether is removed by evaporation under reduced pressure until a solution of about 2 ml
  11. customhas been obtained
  12. customto yield
  13. temperatureafter cooling
  14. customa solid which is isolated by filtration
  15. customThe solid collected in that manner
  16. additionis added to a solution of potassium hydroxide (380 mg)
  17. dissolutiondissolved in a water/methanol mixture (1 ml/10 ml)
  18. temperatureThe solution is refluxed for 12 hours
  19. temperaturecooled
  20. concentrationconcentrated under reduced pressure
  21. extractionextracted 3 times with water
  22. dry with materialThe organic phase is dried over magnesium sulphate
  23. filtrationfiltered
  24. concentrationconcentrated under reduced pressure
  25. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-5bb1c8f02f7c46e9a221fdec341aef83
Source dataset
uspto-grants-2001_11
Patent number
US06319930B1

Reaction notes

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