Acetic Acid → HCID 22908988, compound

HRID 574126Notes

Reaction equation

HRID 574126 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5](=[O:11])[N:6]([CH2:9][CH3:10])[C:7]=1[NH2:8].[CH2:15]([OH:17])[CH3:16].[OH-].[Na+].C(O)(=O)C>C(O)(=O)CO.O>[CH2:12]([N:4]1[C:3](=[O:14])[C:2]2[NH:1][C:16]([CH2:15][OH:17])=[N:8][C:7]=2[N:6]([CH2:9][CH3:10])[C:5]1=[O:11])[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 45721335,6-Diamino-1,3-diethyluracil

Product 1

HCID 22908988HCID 22908988, compound

Reagents, catalysts & solvents 2

HCID 757Glycolic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

2.1 grams of 5,6-diamino-1,3-diethyluracil were stirred in 3.4 grams glycolic acid for 1 hour at 100° C. A 1:1 solution of ethanol and water (20 ml) was thereafter added to the cooled and stirred mixture, followed by the addition of 8 grams of sodium hydroxide in 30 ml water, which raised the pH to above 12. The solution was then refluxed for 2.5 hours, cooled, 30 ml acetic acid was added, and the mixture was then cooled overnight at 4° C. The resulting precipitate was collected and dried, to give 1,3-diethyl-8-hydroxymethylxanthine (1.5 gram).

Workup

  1. temperaturecooled
  2. temperatureraised the pH to above 12
  3. temperatureThe solution was then refluxed for 2.5 hours
  4. temperaturecooled
  5. customThe resulting precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-b57351a98cf24609ba12951f167486be
Source dataset
uspto-grants-2015_05
Patent number
US09034872B2

Reaction notes

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