Ammonia → HCID 21548008, compound

HRID 1604874Notes

Reaction equation

HRID 1604874 reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[N:4][C:5]([C:9]#[N:10])=[C:6]([NH2:8])[N:7]=1.[OH-:13].[Na+].N.[OH2:16]>>[NH2:1][C:2]1[C:3]([C:11](=[O:16])[NH2:12])=[N:4][C:5]([C:9](=[O:13])[NH2:10])=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 14798Sodium HydroxideHCID 19022925HCID 19022925, compound

Product 1

HCID 21548008HCID 21548008, compound

Procedure

A slurry consisting of 7.00 g (43.8 mmol) of 3,5-diamino-2,6-dicyanopyrazine in 1.2l of water in which was dissolved 3.50 g (97.6 mol) of sodium hydroxide was heated rapidly to reflux. The reaction mixture became homogeneous within 3 min at reflux, followed in 1 min by the precipitation of 3,5-diamino-2,6-dicarbamoylpyrazine. After a total of 3 hr 10 min at reflux a homogeneous solution was again obtained. Reflux was continued for an additional 40 min as a stream of nitrogen was passed through the reaction medium to eliminate any residual ammonia. Cooling in an ice bath resulted in the precipitation of 3.30 g (16.9 mmol) of 3,5-diamino-2,6-dicarbamoylpyrazine which was collected by filtration and oven dried. Acidification of the filtrate to pH 3 with hydrochloric acid gave 5.00 g (24.4 mmol) of 3,5-diamino-6-carbamoylpyrazinoic acid after collection by filtration and oven drying. This represents a 61% conversion and 94% yield of the amide acid.

Workup

  1. temperaturewas heated rapidly
  2. temperatureto reflux
  3. temperatureat reflux
  4. customfollowed in 1 min by the precipitation of 3,5-diamino-2,6-dicarbamoylpyrazine
  5. temperatureAfter a total of 3 hr 10 min at reflux a homogeneous solution
  6. customwas again obtained
  7. temperatureReflux
  8. waitwas continued for an additional 40 min as a stream of nitrogen
  9. temperatureCooling in an ice bath

Sources & evidence

ORD record
ord-eae79ddbccf84cdfb52990a07e4ef913
Source dataset
uspto-grants-1976_04
Patent number
US03948895

Reaction notes

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