Sodium Hydroxide → 7-(5-Hydroxy-5-methylhexyl)-3-methylxanthine

HRID 1762535Notes

Reaction equation

HRID 1762535 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].[OH-].[Na+].Cl[CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:23])([CH3:22])[CH3:21]>CN(C)C=O>[OH:23][C:20]([CH3:22])([CH3:21])[CH2:19][CH2:18][CH2:17][CH2:16][N:7]1[C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 706393-MethylxanthineHCID 137476791-Chloro-5-hydroxy-5-methylhexane

Product 1

HCID 137476807-(5-Hydroxy-5-methylhexyl)-3-methylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

83 g (0.5 mol) of 3-methylxanthine are dissolved in 500 ml of 1N sodium hydroxide solution (0.5 mol) under the influence of heat. The mixture is filtered, the water is distilled off under reduced pressure and the sodium salt which remains is dried under a high vacuum. After addition of 1.5 liters of dimethylformamide and 75.3 g (0.5 mol) of 1-chloro-5-hydroxy-5-methylhexane, the mixture is heated at 110° C. for 6 hours, while stirring, filtered hot and evaporated under reduced pressure, the residue obtained is taken up in 1 liter of hot 1N sodium hydroxide solution, the hot solution is filtered and, after cooling to room temperature, 6N hydrochloric acid is added dropwise, with stirring, until a pH of 9 is reached. The precipitate is filtered off with suction, washed neutral and dried in vacuo.

Workup

  1. temperatureof heat
  2. filtrationThe mixture is filtered
  3. distillationthe water is distilled off under reduced pressure
  4. dry with materialthe sodium salt which remains is dried under a high vacuum
  5. filtrationfiltered hot
  6. customevaporated under reduced pressure
  7. customthe residue obtained
  8. filtrationthe hot solution is filtered
  9. temperatureafter cooling to room temperature
  10. addition6N hydrochloric acid is added dropwise
  11. stirringwith stirring, until a pH of 9
  12. filtrationThe precipitate is filtered off with suction
  13. washwashed neutral
  14. customdried in vacuo

Sources & evidence

ORD record
ord-bc9497aaf57043adbf80ce262f868ba1
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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