Benzyl Bromide → 7-Benzyl-3-methylxanthine

HRID 1762540Notes

Reaction equation

HRID 1762540 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[C:7](=[O:13])[NH:6][C:5]1=[O:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.CO>[CH2:15]([N:9]1[C:8]2[C:7](=[O:13])[NH:6][C:5](=[O:14])[N:4]([CH3:3])[C:12]=2[N:11]=[CH:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 706393-Methylxanthine

Product 1

HCID 6856307-Benzyl-3-methylxanthine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

20 g (0.5 mol) of sodium hydroxide dissolved in 200 ml of water are added to a suspension of 83 g (0.5 mol) of 3-methylxanthine in 500 ml of methanol, the mixture is stirred at 70° C. for one hour, 85.5 g (0.5 mol) of benzyl bromide are then added dropwise at the same temperature and the reaction mixture is kept between 70° and 80° C. for 5 hours. It is then cooled and filtered cold with suction, the product on the suction filter is washed with water and dissolved in 1000 ml of 1N sodium hydroxide solution under the influence of heat, the solution is filtered and the pH is brought slowly to 9.5 with 4N hydrochloric acid, while stirring. The crystals are filtered off from the still warm solution, washed with water until free from chloride and dried in vacuo.

Workup

  1. waitthe reaction mixture is kept between 70° and 80° C. for 5 hours
  2. temperatureIt is then cooled
  3. filtrationfiltered cold with suction
  4. filtrationthe product on the suction filter
  5. washis washed with water
  6. dissolutiondissolved in 1000 ml of 1N sodium hydroxide solution under the influence
  7. temperatureof heat
  8. filtrationthe solution is filtered
  9. stirringwhile stirring
  10. filtrationThe crystals are filtered off from the still warm solution
  11. washwashed with water until free from chloride
  12. customdried in vacuo

Sources & evidence

ORD record
ord-e627e659c3534a59b1c6945e5d48f246
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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