Acetic Anhydride → Lcb-2183

HRID 1681008Notes

Reaction equation

HRID 1681008 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([NH2:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[C:11]([O:14][C:15](=O)[CH3:16])(=O)[CH3:12]>>[CH2:11]([O:14][CH2:15][C:16]1[NH:10][C:8](=[O:9])[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[N:1]=1)[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 280292Aminopyrazine carboxamide

Product 1

HCID 135418284Lcb-2183

Procedure

A mixture of 8.3 g (0.060 mole) of 3-amino-2-pyrazinecarboxamide [prepared according to R. C. Ellingson et al., J. Am. Chem. Soc. 1945, 67, 1711], 49.5 g (0.24 mole) of triethyl orthoethoxyacetate [prepared according to S. M. McElvain and P. M. Walters, J. Am. Chem. Soc. 1942, 64, 1963] and 53 ml of acetic anhydride is refluxed under a nitrogen atmosphere for 3 hours. The temperature of this reflux falls with the passage of time from 124° and 96° C. and then remains constant at the latter temperature. After cooling, the precipitate formed is isolated by filtration. Yld: 5.5 g (44%) m.p. 168°-169° C.

Workup

  1. temperatureis refluxed under a nitrogen atmosphere for 3 hours
  2. customfalls with the passage of time from 124° and 96° C.
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. customis isolated by filtration

Sources & evidence

ORD record
ord-9282484f76ad4961b3e84ea8bc9ac9b2
Source dataset
uspto-grants-1992_12
Patent number
US05167949

Reaction notes

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