Hydrochloric Acid → 5-Nitroso-4,6-pyrimidinediamine

HRID 260153Notes

Reaction equation

HRID 260153 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[N:7]=[CH:6][N:5]=1.[N:11]([O-])=[O:12].[Na+].C([O-])(O)=O.[Na+]>O>[NH2:3][C:4]1[C:9]([N:11]=[O:12])=[C:8]([NH2:10])[N:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 796074,6-Pyrimidinediamine, monohydrochloride2×HCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 2597525-Nitroso-4,6-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 250 mL of 2N HCl was added 8.0 g (55 mmoles) of 4,6-diaminopyrimidine hydrochloride (34). The 4,6-diamino-pyrimidine hydrochloride was allowed to dissolve. The solution was then cooled to 0° C. and a solution of 4.2 g (61 mmoles) of NaNO2 dissolved in 15 mL of H2O was added dropwise within 20 minutes while stirring. Stirring was continued for another 30 minutes at 0° and then 2 hours at room temperature. The violet solution was neutralized by NaHCO3, the precipitate collected, washed with H2O and ethanol and dried to give 35 as 6.3 g (82% yield) of a blue-violet crystal powder (m.p. >350° C.).

Workup

  1. dissolutionto dissolve
  2. additionwas added dropwise within 20 minutes
  3. stirringStirring
  4. custom2 hours
  5. customat room temperature
  6. customthe precipitate collected
  7. washwashed with H2O and ethanol
  8. customdried

Sources & evidence

ORD record
ord-6993103a2b0e41168432bd578e38b283
Source dataset
uspto-grants-1996_06
Patent number
US05525711

Reaction notes

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