Ethanol → HCID 178470302, compound

HRID 2237875Notes

Reaction equation

HRID 2237875 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7](N)=[O:8].[CH2:10]([OH:12])[CH3:11]>CS(O)(=O)=O>[CH2:10]([O:12][C:7]([C:3]1[N:4]=[CH:5][NH:6][C:2]=1[NH2:1])=[O:8])[CH3:11]

Participants

4

Reactant 2

HCID 702EthanolHCID 96795-Aminoimidazole-4-carboxamide

Product 1

HCID 178470302HCID 178470302, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A stirred solution of commercially available 5-amino-1H-imidazole-4-carboxamide (25 g, 198 mmol) in methanesulfonic acid (107 mL) and ethanol (400 mL) was stirred at reflux conditions for 12d, evaporated and water (300 mL) was added. While stirring and cooling (ice/water) sodium hydroxide solution (32%) was added until pH=6 was reached. The water layer was saturated with sodium chloride and extracted with ethyl acetate (3×200 mL). The combined organic layers were dried (MgSO4), evaporated and the crude product purified crystallization (ethyl acetate/ethanol) to yield 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (13.7 g, 45%) as a light brown solid. MS (EI) 155.1 [(M)+]; mp 178° C.

Workup

  1. customevaporated
  2. additionwater (300 mL) was added
  3. temperaturecooling (ice/water) sodium hydroxide solution (32%)
  4. additionwas added until pH=6
  5. extractionextracted with ethyl acetate (3×200 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customevaporated
  8. customthe crude product purified
  9. customcrystallization (ethyl acetate/ethanol)

Sources & evidence

ORD record
ord-43a1f6e04566450ca04ee9f71ba78eaa
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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