Nitric Acid → 6-Chloro-1,3-dimethyl-5-nitropyrimidine-2,4(1h,3h)-dione

HRID 463296Notes

Reaction equation

HRID 463296 reaction equation
[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>>[Cl:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 2496456-Chloro-1,3-dimethyl-5-nitropyrimidine-2,4(1h,3h)-dione

Procedure

To 25 ml of surfuric acid was gradually added 8.5 g (0.049 mol) of 6-chloro-1,3-dimethyluracil as described in Synthesis Example 1. To the solution was gradually added at 0° to 5° C. 8.5 ml of fuming nitric acid and the mixture was stirred for 5 minutes. The reaction solution was poured onto ice and extracted twice with chloroform. The organic layer was dried with anhydrous magnesium sulfate, concentrated and the crystals thus-obtained were recrystallized from a solvent mixture of ethyl acetate and hexane to obtain 7.5 g of 6-chloro-1,3-dimethyl-5-nitrouracil.

Workup

  1. customas described in Synthesis Example 1
  2. additionTo the solution was gradually added at 0° to 5° C
  3. additionThe reaction solution was poured onto ice
  4. extractionextracted twice with chloroform
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe crystals thus-obtained
  8. customwere recrystallized from a solvent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-840f167555b84ce2a3306e946df53d77
Source dataset
uspto-grants-1985_05
Patent number
US04518685

Reaction notes

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