Ethanol → 9-(5-Carboxypentyl)-1,3-dimethylxanthine

HRID 484638Notes

Reaction equation

HRID 484638 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[N:15]([CH3:16])[C:14](=[O:17])[N:13]([CH3:18])[C:12](=[O:19])[C:11]=1[NH:20][CH:21]=O)([OH:3])=[O:2].C(O)C>ClC1C=CC=CC=1Cl>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH:21]=[N:20][C:11]2[C:12](=[O:19])[N:13]([CH3:18])[C:14](=[O:17])[N:15]([CH3:16])[C:10]1=2)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 702EthanolHCID 13337060HCID 13337060, compound

Product 1

HCID 133370619-(5-Carboxypentyl)-1,3-dimethylxanthineYield 66%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

9.3 Grams (0.03 mol) of the formamido derivative (IV) was suspended in 500 ml of o-dichlorobenzene and stirred at reflux under an inert atmosphere for 4 hours. It was cooled and the solvent removed on a rotary evaporator attached to a vacuum pump. The crystalline residue was partitioned between 200 ml of ether and 100 ml of 5% aqueous sodium bicarbonate solution. The aqueous phase was separated, washed with 100 ml of ether, and acidified to pH 3.2 with 5N HCl. The precipitate was recrystallized first from aqueous methanol, then from absolute ethanol to give 5.8 g (66% yield) of the xanthine (V) as fine white crystals, mp 177° C.

Workup

  1. temperatureat reflux under an inert atmosphere for 4 hours
  2. temperatureIt was cooled
  3. customthe solvent removed on a rotary evaporator
  4. customThe crystalline residue was partitioned between 200 ml of ether and 100 ml of 5% aqueous sodium bicarbonate solution
  5. customThe aqueous phase was separated
  6. washwashed with 100 ml of ether
  7. customThe precipitate was recrystallized first from aqueous methanol

Sources & evidence

ORD record
ord-b90d2810f23d420ebbcb5e8b25ff5c78
Source dataset
uspto-grants-1985_08
Patent number
US04533493

Reaction notes

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