Nitric Acid → HCID 58035654, compound

HRID 1423339Notes

Reaction equation

HRID 1423339 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6](S)[N:7]([C:9]3[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=3)[C:14]([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH:8]=2)[CH2:3][CH2:2]1.[N+]([O-])(O)=O>O>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=3)[C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[O:15])[CH:8]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178459394HCID 178459394, compound

Product 1

HCID 58035654HCID 58035654, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Isopropyl 5-(4-cyclopropyl-2-mercapto-1H-imidazol-1-yl)-2-fluorobenzoate (0.776 g, 2.43 mmol) was suspended in a water (16 ml) and fuming nitric acid (4 ml) mixture. The mixture was stirred under nitrogen at 100° C. while monitoring by LC/MS. When the reaction was complete heat was removed and ammonium hydroxide was added to bring the pH to neutral. The solvent was removed under reduced pressure and the residue purified by column chromatography to afford isopropyl 5-(4-cyclopropyl-1H-imidazol-1-yl)-2-fluorobenzoate. (0.306 g, 1.06 mmol). 44% yield. 289 (M+1).

Workup

  1. temperatureWhen the reaction was complete heat
  2. customwas removed
  3. additionammonium hydroxide was added
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-41d417bb6ef240edb344a68ff47a3af8
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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