Hydrochloric Acid → 5-Nitroso-2,4,6-pyrimidinetriamine

HRID 1762226Notes

Reaction equation

HRID 1762226 reaction equation
[N:1]([O-:3])=O.[Na+].[C:5](#[N:9])[CH2:6][C:7]#[N:8].Cl.[NH2:11][C:12]([NH2:14])=[NH:13].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C)C=O>[N:1]([C:6]1[C:5]([NH2:9])=[N:13][C:12]([NH2:14])=[N:11][C:7]=1[NH2:8])=[O:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5742Guanidine HydrochlorideHCID 8010MalononitrileHCID 10340Sodium CarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 705045-Nitroso-2,4,6-pyrimidinetriamineYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 70 g of sodium nitrite in 120 g of water was added dropwise at room temperature to a suspension of 66 g of malononitrile and 96 g of guanidine hydrochloride in 200 g of water, and the pH was kept at 4 by the addition of hydrochloric acid. After the reaction had continued for 4 hours at room temperature, 21 g of sodium carbonate and 400 g of dimethylformamide were added. The water was distilled off under reduced pressure. Thereafter, the reaction mixture was heated at 140° C. for 1 hour, isomerization to 5-nitroso-2,4,6-triamino-pyrimidine taking place. After the reaction was complete, 400 ml of water were added, and the product was filtered off and washed with water. After the product had been dried, 140 g of a pure raspberry-red 5-nitroso-2,4,6-triaminopyrimidine were obtained. The melting point of the product was above 340° C. and the yield was 91 percent.

Workup

  1. distillationThe water was distilled off under reduced pressure
  2. addition400 ml of water were added
  3. filtrationthe product was filtered off
  4. washwashed with water
  5. customAfter the product had been dried

Sources & evidence

ORD record
ord-23c0f39b4120411d90c15cad7efc8c69
Source dataset
uspto-grants-1989_05
Patent number
US04831139

Reaction notes

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