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

HRID 648886Notes

Reaction equation

HRID 648886 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[N:12]([CH3:13])[C:11](=[O:14])[N:10]([CH3:15])[C:9](=[O:16])[CH:8]=1.[N+:17]([O-])([OH:19])=[O:18]>>[Cl:6][C:7]1[N:12]([CH3:13])[C:11](=[O:14])[N:10]([CH3:15])[C:9](=[O:16])[C:8]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric 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)-dioneYield 70%

Procedure

To 25 ml of sulfuric acid was slowly added 8.5 g (0.049 mol) of 6-chloro-1,3-dimethyluracil as prepared in Synthesis Example 1 at 10° to 15° C. To this solution was gradually added 8.5 ml of fuming nitric acid at 0° to 5° C. After stirring for 5 minutes, the reaction mixture was poured onto ice and extracted twice with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The resulting crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give 7.5 g (70%) of 6-chloro-1,3-dimethyl-5-nitrouracil having a melting point of 91° to 92° C.

Workup

  1. customas prepared in Synthesis Example 1 at 10° to 15° C
  2. customat 0° to 5° C
  3. additionthe reaction mixture was poured onto ice
  4. extractionextracted twice with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting crystals were recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a25819ccd7b148d29581118983822033
Source dataset
uspto-grants-1988_04
Patent number
US04737442

Reaction notes

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