Water → HCID 15574685, compound

HRID 1577821Notes

Reaction equation

HRID 1577821 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:6]=2[C:5](=[O:21])[NH:4][C:3]1=[O:22].[OH2:23].[OH-].[Na+]>CO>[O:23]=[C:12]([CH3:11])[CH2:13][CH2:14][CH2:15][CH2:16][N:4]1[C:5](=[O:21])[C:6]2[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 15574684HCID 15574684, compound

Product 1

HCID 15574685HCID 15574685, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

80.3 g of 3-methyl-7-n-decyl-xanthine, 140 g of water, 90 g of methanol, 10 g of sodium hydroxide and 44.6 g of 1-bromohexanone-(5) are boiled under reflux for 4 hours. After acidification with 2 ml of concentrated sulphuric acid, the reaction mixture is filtered hot to remove the unreacted 3-methyl-7-n-decyl-xanthine and the filtrate is worked up as in Example 1. 66.1 g of a crude crystalline product are obtained and are recrystallised from 500 ml of diisopropyl ether. The 1-(5-oxohexyl)-3-methyl-7-(n-decyl)-xanthine which is obtained in 85% yield melts at 64°-66° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationAfter acidification with 2 ml of concentrated sulphuric acid, the reaction mixture is filtered hot
  3. customto remove the unreacted 3-methyl-7-n-decyl-xanthine
  4. custom66.1 g of a crude crystalline product are obtained
  5. customare recrystallised from 500 ml of diisopropyl ether

Sources & evidence

ORD record
ord-c854b1e8889e4a5c817d771c2b0071a4
Source dataset
uspto-grants-1981_09
Patent number
US04289776

Reaction notes

Loading…