Nitric Acid → HCID 14276966, compound

HRID 1164729Notes

Reaction equation

HRID 1164729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[CH:10]=[N:9]2)=[C:4]([F:17])[CH:3]=1.[N+:18]([O-])([OH:20])=[O:19]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:18]([O-:20])=[O:19])=[CH:6][C:5]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[CH:10]=[N:9]2)=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14276940HCID 14276940, compound

Product 1

HCID 14276966HCID 14276966, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a stirred solution of 24.7 g (0.097 mole) of 2-(4-chloro-2-fluorophenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione in 30 mL of concentrated sulfuric acid was added dropwise a mixture of 70 mL of concentrated sulfuric acid and 100 mL of fuming nitric acid. The reaction mixture temperature was kept below 40° C. during the addition. Upon completion of addition the reaction mixture was stirred at ambient temperature for four hours. The reaction mixture was poured into ice-water and the mixture extracted with ethyl acetate. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield a solid. The solid was triturated with diethyl ether and collected by filtration to yield 20.6 g of 2-(4-chloro-2-fluoro-5-nitrophenyl)-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione.

Workup

  1. additionThe reaction mixture temperature was kept below 40° C. during the addition
  2. additionUpon completion of addition the reaction mixture
  3. extractionthe mixture extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto yield a solid
  8. customThe solid was triturated with diethyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-321a48b015f34385a8b2ee583d7dd91a
Source dataset
uspto-grants-1990_03
Patent number
US04906287

Reaction notes

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