Hydrochloric Acid → 5-Chloro-6-(3-nitro-1,2,4-triazol-1-ylmethyl)uracil

HRID 1274891Notes

Reaction equation

HRID 1274891 reaction equation
[N+:1]([C:4]1[N:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].[Cl:9][C:10]1[C:11](=[O:19])[NH:12][C:13](=[O:18])[NH:14][C:15]=1[CH2:16]Cl.Cl>[OH-].[K+]>[Cl:9][C:10]1[C:11](=[O:19])[NH:12][C:13](=[O:18])[NH:14][C:15]=1[CH2:16][N:6]1[CH:7]=[N:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 41710565-Chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 178526901HCID 178526901, compound

Product 1

HCID 216993145-Chloro-6-(3-nitro-1,2,4-triazol-1-ylmethyl)uracilYield 73%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.88 g of 3-nitro-1,2,4-triazole in a 1 N aqueous solution of KOH (10 ml), 0.50 g of 5-chloro-6-chloromethyluracil was added, followed by heating at 80° C. for 2.5 hours under stirring. The reaction mixture was neutralized with 6 N hydrochloric acid. A precipitate was collected by filtration and then washed with water and methanol, whereby 510 mg of the title compound were obtained (yield: 73%).

Workup

  1. filtrationA precipitate was collected by filtration
  2. washwashed with water and methanol

Sources & evidence

ORD record
ord-aabb89646ec84ddabc29689d3d85b816
Source dataset
uspto-grants-2000_12
Patent number
US06159969

Reaction notes

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