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

HRID 1462593Notes

Reaction equation

HRID 1462593 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 5 N HCl. The precipitate was recrystalllized 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

Sources & evidence

ORD record
ord-3fbef2c91b97452f8aaf82843246d355
Source dataset
uspto-grants-1984_07
Patent number
US04460772

Reaction notes

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