Potassium Nitrate → HCID 23297991, compound

HRID 1953788Notes

Reaction equation

HRID 1953788 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[CH3:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=1[NH:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>S(=O)(=O)(O)O>[CH3:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]=1[NH:17][C:18](=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 23298019HCID 23298019, compound

Product 1

HCID 23297991HCID 23297991, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

14.4 g (142.3 mmol) of potassium nitrate are added in small portions to an ice-cooled solution of 32.6 g (118.6 mmol) of ethyl N-(2-methyl-4-trifluoromethylphenyl)oxamate in concentrated sulfuric acid. After stirring at 0° C. for 1.5 hours, the mixture is cautiously poured onto 900 g of ice. The white suspension is extracted with ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated under reduced pressure in a rotary evaporator. Crystallization from ethyl acetate/hexane affords 35.5 g of the title compound as white crystals.

Workup

  1. extractionThe white suspension is extracted with ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure in a rotary evaporator
  5. customCrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ae29c5010466402ca82f3980c074eda1
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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