Sulfuric Acid → 6-Amino-2-(ethoxymethyl)-5-nitroso-4(3H)-pyrimidinone

HRID 326873Notes

Reaction equation

HRID 326873 reaction equation
[N:1]([O-:3])=O.[Na+].[NH2:5][C:6]1[N:11]=[C:10]([CH2:12][O:13][CH2:14][CH3:15])[NH:9][C:8](=[O:16])[CH:7]=1.[OH-].[Na+].S(=O)(=O)(O)O>O>[NH2:5][C:6]1[N:11]=[C:10]([CH2:12][O:13][CH2:14][CH3:15])[NH:9][C:8](=[O:16])[C:7]=1[N:1]=[O:3]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 1354566226-amino-2-(ethoxymethyl)-4(3H)-pyrimidinone

Product 1

HCID 1354111536-Amino-2-(ethoxymethyl)-5-nitroso-4(3H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.7 g (0.256 mole) of sodium nitrite are added to a solution of 39.5 g (0.233 mole) of 6-amino-2-(ethoxymethyl)-4(3H)-pyrimidinone in 336 ml (0.336 mole) of 1N sodium hydroxide. A solution of 17.9 ml (0.320 mole) of 96% sulphuric acid diluted in 179 ml of water is then added dropwise at between 0° and 5° C. The precipitate formed is isolated by filtration immediately after completion of the addition. The solid obtained is washed with cold water and then with ethyl ether. After drying, it is used in the next step without further purification. Yld: 46.2 g (quantitative), m.p. 163°-165° C. An analytical sample was obtained by recrystallization from methanol. M.p. 166°-167° C.

Workup

  1. additionis then added dropwise at between 0° and 5° C
  2. customThe precipitate formed
  3. customis isolated by filtration
  4. additionimmediately after completion of the addition
  5. customThe solid obtained
  6. washis washed with cold water
  7. customAfter drying
  8. customit is used in the next step without further purification
  9. customAn analytical sample was obtained by recrystallization from methanol

Sources & evidence

ORD record
ord-8e4b81642d154b289142469d7aac59e5
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Reaction notes

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