Acetic Acid → HCID 178437205, compound

HRID 1494507Notes

Reaction equation

HRID 1494507 reaction equation
C(O[CH:4]=[C:5]([CH2:8][CH3:9])[C:6]#[N:7])C.[NH2:10][C:11]([NH2:13])=[O:12].CC[O-].[Na+].C(O)(=O)C>C1(C)C(C)=CC=CC=1>[CH2:8]([C:5]1[C:6]([NH2:7])=[N:10][C:11](=[O:12])[NH:13][CH:4]=1)[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1176UreaHCID 2723922Sodium ethoxideHCID 54138132HCID 54138132, compound

Product 1

HCID 178437205HCID 178437205, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

25 g (0.2 mol) of 3-ethoxy-2-ethyl-acrylonitrile were added over a period of 1 hour to a refluxing mixture of 15.6 g (0.26 mol) of urea and 15.7 g (0.23 mol) of sodium ethylate in 50 g of xylene, and the resulting mixture was heated for 3 additional hours at its boiling point. Thereafter, the ethanol in the reaction mixture was distilled off, and the residue was taken up in 120 g of water. The aqueous phase was separated and admixed with 13.8 g (0.23 mol) of acetic acid. The precipitated product was collected by suction filtration and recrystallized from water in the presence of activated charcoal. 18.4 g (66.3% of theory) of pure 5-ethyl-cytosine were obtained.

Workup

  1. temperaturethe resulting mixture was heated for 3 additional hours at its boiling point
  2. distillationThereafter, the ethanol in the reaction mixture was distilled off
  3. customThe aqueous phase was separated
  4. filtrationThe precipitated product was collected by suction filtration
  5. customrecrystallized from water in the presence of activated charcoal

Sources & evidence

ORD record
ord-85bd96fe0da647c5b1167a9e3074dd01
Source dataset
uspto-grants-1991_06
Patent number
US05026852

Reaction notes

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