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

HRID 464603Notes

Reaction equation

HRID 464603 reaction equation
[NH2:1][C:2]1[N:7]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6](=[O:13])[NH:5][C:4](=[O:14])[CH:3]=1.Cl.[N:16]([O-])=[O:17].[Na+]>O>[NH2:1][C:2]1[N:7]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6](=[O:13])[NH:5][C:4](=[O:14])[C:3]=1[N:16]=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 219585496-Amino-1-cyclopentyl-1,3-dihydropyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 219585066-Amino-1-cyclopentyl-5-nitroso-2,4(1h,3h)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

12.4 g (0.064 mol) of 6-amino-1-cyclopentyl-2,4-(1H,3H)-pyrimidinedione (XIV) was suspended in 200 ml water. To this was added 14 ml of 5N HCl and 4.8 g of NaNO2 (0.07 mol) which was dissolved in water. The reaction mixture was stirred for 1 hour and washed with water. Yield 12.9 g (90%) (XV) NMR.

Workup

  1. washwashed with water

Sources & evidence

ORD record
ord-8555b679fcc141958fbd7bc427692110
Source dataset
uspto-grants-1985_10
Patent number
US04548818

Reaction notes

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