Hydrochloric Acid → 6-Amino-1-cyclopropyl-5-nitroso-2,4(1H,3H)-pyrimidinedione

HRID 464596Notes

Reaction equation

HRID 464596 reaction equation
[NH2:1][C:2]1[N:7]([CH:8]2[CH2:10][CH2:9]2)[C:6](=[O:11])[NH:5][C:4](=[O:12])[CH:3]=1.Cl.[N:14]([O-])=[O:15].[Na+]>O>[NH2:1][C:2]1[N:7]([CH:8]2[CH2:10][CH2:9]2)[C:6](=[O:11])[NH:5][C:4](=[O:12])[C:3]=1[N:14]=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 71315486-Amino-1-cyclopropyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 542234936-Amino-1-cyclopropyl-5-nitroso-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

31.7 g (0.19 mol) of 6-amino-1-cyclopropyl-2,4-(1H,3H)-pyrimidinedione (II) was suspended in 250 ml water. To this was added 45 ml of 5N HCl and 15 g of NaNO2 (0.22 mol) which was dissolved in water. The reaction mixture was stirred for 2 hours and after cooling, the red crystals were filtered off and washed with water. Yield 31.9 g (86%) (III) NMR.

Workup

  1. temperatureafter cooling
  2. filtrationthe red crystals were filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-23f0ec4a203c41439a804afeacc0a235
Source dataset
uspto-grants-1985_10
Patent number
US04548818

Reaction notes

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