Theophylline → 7-(6-Bromohexyl)-1,3-dimethylxanthine

HRID 482880Notes

Reaction equation

HRID 482880 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].[OH-].[Na+].[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>O.C(O)CC>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][N:9]1[C:10]2[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:13])[C:6]=2[N:7]=[CH:8]1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 202440737-(6-Bromohexyl)-1,3-dimethylxanthine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

1,3-dimethylxanthine is dissolved in a mixture of 250 ml of water and 750 ml of n-propanol by adding an equimolar quantity of sodium hydroxide and heating. An equivalent amount of 1,6-dibromohexane is quickly added to the solution and the mixture is boiled under reflux for 1 hour. After evaporation of the n-propanol, 7-(6-bromohexyl)-1,3-dimethylxanthine is isolated.

Workup

  1. temperatureheating
  2. temperatureunder reflux for 1 hour
  3. customAfter evaporation of the n-propanol

Sources & evidence

ORD record
ord-6d3bcbb674b14df191e141ce8b413deb
Source dataset
uspto-grants-1986_03
Patent number
US04576947

Reaction notes

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