Acetic Acid → 6-Amino-3-methyl-5-nitroso-1-phenylpyrimidine-2,4(1H,3H)-dione

HRID 2258471Notes

Reaction equation

HRID 2258471 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1.[OH-].[Na+].[N:19]([O-])=[O:20].[Na+].C(O)(=O)C>O>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[C:3]=1[N:19]=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 16492566-Amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 127062666-Amino-3-methyl-5-nitroso-1-phenylpyrimidine-2,4(1H,3H)-dioneYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The obtained 6-amino-3-methyl-1-phenyluracil (24 g, 0.11M) and NaOH (2.8 g, 70 mM) were dissolved in 110 ml of water. To the resulting solution was added dropwise an aqueous solution of sodium nitrite (9.5 g/80 ml). Acetic acid (13 ml) was then added dropwise at 0° C. and the mixture was brought to room temperature, followed by stirring for 2 hours. A precipitated solid product was obtained by filtration. The solid product was washed successively with water and methanol and dried to yield 6-amino-3-methyl-5-nitroso-1-phenyluracil (yield: 27 g, or 99% based on 6-amino-3-methyl-1-phenyluracil).

Workup

  1. customwas brought to room temperature
  2. customA precipitated solid product was obtained by filtration
  3. washThe solid product was washed successively with water and methanol
  4. customdried

Sources & evidence

ORD record
ord-749580c4ed5446eba1aae9dfa34d8a4b
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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