Benzyl Chloride → 7-Benzyl-3-methylxanthine

HRID 1995

Reaction equation

HRID 1995 reaction equation
[H-].[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].[H][H].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.O>[CH2:17]([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:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 706393-MethylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 6856307-Benzyl-3-methylxanthine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

16.8 g (0.7 mol) of sodium hydride were introduced in portions with stirring into a suspension of 99.6 g (0.6 mol) of 3-methylxanthine in 1.5 l of dimethylformamide. After evolution of hydrogen had ended, the mixture was heated to 100° C., treated dropwise with 76 g (0.6 mol) of benzyl chloride and heated at 120° C. for a further 6 hours. The reaction mixture was cooled and cautiously poured into 3 l of water. The solid was filtered off with suction and washed with water, the filter residue was taken up in ethanol and the solution was stirred at room temperature for one hour. The crystallizate was filtered, washed with ethanol and dried under reduced pressure.

Workup

  1. temperatureheated at 120° C. for a further 6 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe solid was filtered off with suction
  4. washwashed with water
  5. filtrationThe crystallizate was filtered
  6. washwashed with ethanol
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b41b35df72e44c4adc18e6e041d2837
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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