Acetic Acid → Uracil, 1,3-diallyl-6-amino-5-nitroso-

HRID 728245

Reaction equation

HRID 728245 reaction equation
[CH2:1]([N:4]1[C:11]([NH2:12])=[CH:10][C:8](=[O:9])[N:7]([CH2:13][CH:14]=[CH2:15])[C:5]1=[O:6])[CH:2]=[CH2:3].C(O)(=O)C.Cl.[N:21]([O-])=[O:22].[Na+]>O>[CH2:1]([N:4]1[C:11]([NH2:12])=[C:10]([N:21]=[O:22])[C:8](=[O:9])[N:7]([CH2:13][CH:14]=[CH2:15])[C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 785661,3-Diallyl-6-aminouracil monohydrateHCID 23668193Sodium Nitrite

Product 1

HCID 572531Uracil, 1,3-diallyl-6-amino-5-nitroso-Yield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-Diallyl-6-aminouracil (5 g) was suspended in 400 ml of water in a 1 L round bottom flask with overhead stirring. Acetic acid (6.7 ml of a 20% solution) was added, followed by intermittent addition of 2 ml of concentrated hydrochloric acid and a sodium nitrite solution (1.53 g in 7 ml water). After 4 hours, this solution was filtered, washed with water, collected and dried in a vacuum oven at 80° C. for 20 hours to yield 4.54 g of 1,3-diallyl-5-nitroso-6-aminouracil as a purple solid, m.p. 170°-180° C. (87% yield).

Workup

  1. filtrationthis solution was filtered
  2. washwashed with water
  3. customcollected
  4. customdried in a vacuum oven at 80° C. for 20 hours

Sources & evidence

ORD record
ord-725fb33edb6248b98506c8b822e078ce
Source dataset
uspto-grants-1991_09
Patent number
US05047534

Linked notes

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