Acetic Anhydride → 1,3-Dimethyl-7-(6-hydroxyhexyl)-xanthine

HRID 462419Notes

Reaction equation

HRID 462419 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)[CH:8]=[N:7][C:6]=2[N:5]([CH3:20])[C:3]1=[O:4].C(OC(=O)C)(=[O:23])C.C([O-])(=O)C.[K+]>C(O)(=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:23])[CH:8]=[N:7][C:6]=2[N:5]([CH3:20])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 202440737-(6-Bromohexyl)-1,3-dimethylxanthine

Product 1

HCID 108027041,3-Dimethyl-7-(6-hydroxyhexyl)-xanthineYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.4 g of 1,3-dimethyl-7-(6-bromohexyl)-xanthine are boiled overnight under reflux in 50 ml of glacial acetic acid to which 1 ml of acetic anhydride and 5 g of potassium acetate have been added. After evaporation of the solvent by distillation in vacuo the residue is dissolved in 50 ml of 5% sulfuric acid on the addition of 20 ml methanol. The solution is boiled under reflux for 1 hour. The mixture is extracted with chloroform. The chloroform phase is washed until it is neutral and concentrated in vacuo. 1,3-dimethyl-7-(6-hydroxyhexyl)-xanthine having a melting point of 80° C. is obtained in a yield of more than 90%.

Workup

  1. additionhave been added
  2. customAfter evaporation of the solvent
  3. distillationby distillation in vacuo the residue
  4. dissolutionis dissolved in 50 ml of 5% sulfuric acid on the addition of 20 ml methanol
  5. temperatureunder reflux for 1 hour
  6. extractionThe mixture is extracted with chloroform
  7. washThe chloroform phase is washed until it
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12e5dc7074e54799aafa39a18c331eb1
Source dataset
uspto-grants-1985_05
Patent number
US04515795

Reaction notes

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