Nitric Acid → HCID 19365489, compound

HRID 849941Notes

Reaction equation

HRID 849941 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][N:19]=1.[N+:26]([O-])([OH:28])=[O:27]>>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[C:10]([N+:26]([O-:28])=[O:27])=[CH:9][C:8]=1[C:14]1[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:21])([F:23])[F:22])=[CH:18][N:19]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 19365488HCID 19365488, compound2×

Product 1

HCID 19365489HCID 19365489, compoundYield 95%

Procedure

To 1.7 ml of concentrated sulfuric acid was added 0.26 g of 3-(2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-332) at 5° C. Furthermore, 85 til of 61% nitric acid was added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was added to ice water, followed by extraction with chloroform. The organic layer was washed with water and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 0.29 g (yield, 95%) of 3-(2,4dichloro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-333; m.p., 114.3° C.).

Workup

  1. customAfter completion of the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7687403a54fd45dcb84ed8c87bd1dc89
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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