Acetic Acid → 1-Butyl-5-nitroso-6-aminouracil

HRID 1380396Notes

Reaction equation

HRID 1380396 reaction equation
[CH2:1]([N:5]1[C:12]([NH2:13])=[CH:11][C:9](=[O:10])[NH:8][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[N:14]([O-])=[O:15].[Na+].C(O)(=O)C>O>[CH2:1]([N:5]1[C:12]([NH2:13])=[C:11]([N:14]=[O:15])[C:9](=[O:10])[NH:8][C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24289966-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 107985701-Butyl-5-nitroso-6-aminouracilYield 84.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

91.5 g (0.5 mole) of 1-butyl-6-aminouracil are suspended in 1 liter of water in a reactor equipped with a magnetic stirrer. A solution of 38 g of sodium nitrite in 250 ml of water is added to the suspension. 65 ml of acetic acid are then run in dropwise with stirring, after which the mixture is stirred for 18 hours at ambient temperature. After cooling in an ice bath, the precipitate is filtered, giving 90 g of violet-coloured crystals.

Workup

  1. customequipped with a magnetic stirrer
  2. stirringafter which the mixture is stirred for 18 hours at ambient temperature
  3. temperatureAfter cooling in an ice bath
  4. filtrationthe precipitate is filtered

Sources & evidence

ORD record
ord-1eb363a8fd5f4bcab6c04d2ec9f97af7
Source dataset
uspto-grants-1986_04
Patent number
US04581451

Reaction notes

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