Sodium borohydride → HCID 18917630, compound

HRID 234056Notes

Reaction equation

HRID 234056 reaction equation
[CH2:1]([C:3]1[S:7][C:6]([N:8]2[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:11][N:10]=[C:9]2[CH2:24]O)=[C:5]([C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH:4]=1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:1]([C:3]1[S:7][C:6]2[N:8]3[C:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N:11][N:10]=[C:9]3[CH2:24][O:35][CH:26]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C:5]=2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18917588HCID 18917588, compound

Product 1

HCID 18917630HCID 18917630, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Ethyl-3-(4-methoxybenzoyl)-2-(3-hydroxymethyl-5-undecyl-1,2,4-triazol-4-yl)thiophene (4.4 g) obtained in Example 20 was dissolved in ethanol (100 ml). Thereto was added sodium borohydride (0.16 g) with stirring and the mixture was stirred at room temperature for 1 hour. After the ethanol was distilled away, 5% aqueous sodium hydrogencarbonate was added thereto and the liberated oily substance was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and toluene (100 ml) was added to the residue. The mixture was refluxed under heating with stirring and sulfuric acid was gradually added dropwise until the reaction ended. After cooling, 5% aqueous sodium hydrogencarbonate was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. After filtration, the residue was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The oily substance obtained was crystallized from hexane to give 1.64 g of 2-ethyl-4-(4-methoxyphenyl)-9-undecyl-4H,6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepine as white crystals, melting point 91°-93° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. distillationAfter the ethanol was distilled away
  3. addition5% aqueous sodium hydrogencarbonate was added
  4. extractionthe liberated oily substance was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure and toluene (100 ml)
  9. additionwas added to the residue
  10. temperatureThe mixture was refluxed
  11. temperatureunder heating
  12. stirringwith stirring
  13. additionsulfuric acid was gradually added dropwise until the reaction
  14. temperatureAfter cooling
  15. addition5% aqueous sodium hydrogencarbonate was added
  16. extractionthe mixture was extracted with ethyl acetate
  17. washThe extract was washed with water
  18. dry with materialdried over anhydrous magnesium sulfate
  19. filtrationAfter filtration
  20. concentrationthe residue was concentrated under reduced pressure
  21. customthe residue was purified by silica gel column chromatography
  22. customThe oily substance obtained
  23. customwas crystallized from hexane

Sources & evidence

ORD record
ord-434fde635ad644cdb4c7b01af86cef36
Source dataset
uspto-grants-1997_01
Patent number
US05593988

Reaction notes

Loading…