Sodium Hydroxide → HCID 20157766, compound

HRID 1706373Notes

Reaction equation

HRID 1706373 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[Na].Br[CH2:22][CH2:23][CH:24]=[CH2:25].[OH-].[Na+]>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[N:12]([CH2:25][CH2:24][CH:23]=[CH2:22])[CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21241Homoallyl bromideHCID 1014211,3-Dibutylxanthine2×HCID 5360545Sodium

Product 1

HCID 20157766HCID 20157766, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

38.9 g of 1,3-di-n-butyl-xanthine are added at 25° C. to a solution of 3.4 g of sodium in 200 ml of absolute ethanol. 20.5 g of 4-bromobut-1-ene are then added at 50° C. After stirring for 46 hours under a nitrogen atmosphere at 70° C. the reaction mixture is cooled to 20° C., precipitated sodium bromide is filtered off and the filtrate is then evaporated under reduced pressure. The residue obtained is treated with chloroform and 1 N sodium hydroxide solution to remove 1,3-di-n-butyl-xanthine. From the chloroform phase there is obtained a yellow oily residue which after column chromatography on silica gel with methylene chloride/acetone (8:2) as eluent and after distillation under reduced pressure yields 29.7 g (78.8% of theory relative to reacted 1,3-di-n-butyl-xanthine) of the title compound with a melting point of 41° to 42° C.

Workup

  1. temperatureis cooled to 20° C.
  2. customprecipitated sodium bromide
  3. filtrationis filtered off
  4. customthe filtrate is then evaporated under reduced pressure
  5. customThe residue obtained
  6. customto remove 1,3-di-n-butyl-xanthine
  7. customFrom the chloroform phase there is obtained a yellow oily residue which after column chromatography on silica gel with methylene chloride/acetone (8:2) as eluent
  8. distillationafter distillation under reduced pressure
  9. customyields

Sources & evidence

ORD record
ord-a09f82ff04d146ce86564c0fbf6d72c5
Source dataset
uspto-grants-1980_06
Patent number
US04207321

Reaction notes

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