Sodium Hydroxide → HCID 14423729, compound

HRID 2165814Notes

Reaction equation

HRID 2165814 reaction equation
[CH2:1]([N:7]1[C:18](=[O:19])[C:17]2[N:15]([CH3:16])[CH:14]=[N:13][C:12]=2[N:10](C)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+]>C(Cl)(Cl)Cl.C(O)C>[CH2:1]([NH:7][C:18]([C:17]1[N:15]([CH3:16])[CH:14]=[N:13][C:12]=1[NH:10][CH3:8])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70569Pentifylline

Product 1

HCID 14423729HCID 14423729, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

Hexyltheobromine (7.5 g) was added to 60 ml of 3N sodium hydroxide, and the mixture was refluxed at elevated temperatures for 6 hours. After the reaction mixture was cooled to ambient temperature, it was extracted with chloroform and the extract was dried and concentrated under reduced pressure to give the residue which in turn was subjected to silica gel column chromatography using a chloroform/ethanol (25:2(v/v)) eluent, thereby yielding 2.6 g (38%) of 5-hexylaminocarbonyl-1-methyl-4-methylaminoimidazole as an oil. A portion of this product was then treated with an ethanolic solution of picric acid to give its picrate.

Workup

  1. temperaturethe mixture was refluxed at elevated temperatures for 6 hours
  2. extractionit was extracted with chloroform
  3. customthe extract was dried
  4. concentrationconcentrated under reduced pressure
  5. customto give the residue which in turn

Sources & evidence

ORD record
ord-e9d9e74cf72c48208f2501844dba8bc8
Source dataset
uspto-grants-1990_07
Patent number
US04942143

Reaction notes

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