4-Toluenesulfonyl chloride → 7-Ethoxymethyl-3-methylxanthine

HRID 1987

Reaction equation

HRID 1987 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C([O-])(=O)C.[Na+].C(O[CH2:20][O:21][CH2:22][CH3:23])C.[CH3:24][N:25]1[C:33]2[N:32]=[CH:31][NH:30][C:29]=2[C:28](=[O:34])[NH:27][C:26]1=[O:35]>CN(C)C=O>[CH2:22]([O:21][CH2:20][N:30]1[C:29]2[C:28](=[O:34])[NH:27][C:26](=[O:35])[N:25]([CH3:24])[C:33]=2[N:32]=[CH:31]1)[CH3:23]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 10024DiethoxymethaneHCID 706393-MethylxanthineHCID 517045Sodium Acetate

Product 1

HCID 137476847-Ethoxymethyl-3-methylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

52.5 g (0.28 mol) of p-toluenesulfonyl chloride were initially introduced into 50 ml of dimethylformamide and 22.6 g (0.29 mol) of sodium acetate were introduced with stirring and ice-cooling. The mixture was subsequently stirred for one hour, treated with 39.1 g of formaldehyde diethyl acetal and again subsequently stirred for one hour. 41.5 g of 3-methylxanthine were then introduced and the reaction mixture was heated at 90° C. for 2 hours. After cooling to 10° C., the precipitated product was filtered off with suction, washed with a little dimethylformamide and washed with demineralized water until chloride-free. The crude product obtained was recrystallized from dimethylformamide.

Workup

  1. additionwere introduced
  2. temperatureice-cooling
  3. stirringThe mixture was subsequently stirred for one hour
  4. stirringagain subsequently stirred for one hour
  5. temperatureAfter cooling to 10° C.
  6. filtrationthe precipitated product was filtered off with suction
  7. washwashed with a little dimethylformamide
  8. washwashed with demineralized water until chloride-free

Sources & evidence

ORD record
ord-d7d7141538f0422c85b05b45f2b6979e
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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