Barbituric Acid → HCID 178514329, compound

HRID 2165902Notes

Reaction equation

HRID 2165902 reaction equation
C(=O)(O)O.[NH2:5][NH:6]C(N)=N.N([O-])=O.[Na+].[NH:14]1[C:21](=[O:22])[CH2:20][C:18](=[O:19])[NH:17][C:15]1=[O:16].Cl.N(C(N)=[NH2+])=[N+]=[N-]>O.Cl>[N+:5](=[C:20]1[C:18](=[O:19])[NH:17][C:15](=[O:16])[NH:14][C:21]1=[O:22])=[N-:6]

Participants

7

Reactant 4

HCID 6211Barbituric AcidHCID 23042627HCID 23042627, compoundHCID 23668193Sodium Nitrite2×HCID 178513185HCID 178513185, compound

Product 1

HCID 178514329HCID 178514329, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

29.9 g (0.22 mol) of aminoguanidine bicarbonate are dissolved in a mixture of 150 ml of water and 54 ml of 10N hydrochloric acid, and the solution is cooled to 0° C. by adding ice. 50 ml of an aqueous solution of sodium nitrite containing 30 g of dissolved sodium nitrite per 100 ml are added dropwise to this mixture in the course of about 15 minutes. After 5 minutes, a nitrite excess which may be present is removed using amidosulphonic acid. 25.6 g (0.2 mol) of barbituric acid are thrown into the solution of azidoformamidinium hydrochloride thus obtained, and the mixture is heated at 70° C. for 4 hours and at 95° for 1 hour. The solution is then cooled down to 0°-5°, the precipitate is filtered off with suction and washed with ice-cold water. Drying at 70° in a through-circulation cabinet gives 27.8 g (90.2%) of diazobarbituric acid of the formula ##STR8##

Workup

  1. additionby adding ice
  2. customa nitrite excess which may be present is removed
  3. customthus obtained
  4. temperaturethe mixture is heated at 70° C. for 4 hours and at 95° for 1 hour
  5. temperatureThe solution is then cooled down to 0°-5°
  6. filtrationthe precipitate is filtered off with suction
  7. washwashed with ice-cold water
  8. customDrying at 70° in a through-circulation cabinet

Sources & evidence

ORD record
ord-e71dab3ef48f4d188284691536cc039c
Source dataset
uspto-grants-1990_07
Patent number
US04942225

Reaction notes

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