Methane → 1-(4-Fluorophenyl)-1H-imidazole-4-carboxylic acid

HRID 860142Notes

Reaction equation

HRID 860142 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C.C>O1CCOCC1.[OH-].[Na+]>[F:17][C:14]1[CH:13]=[CH:12][C:11]([N:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[CH:8]2)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 17390092HCID 17390092, compound

Product 1

HCID 173900481-(4-Fluorophenyl)-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Crude 1-(4-fluoro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (175 mmol) was dissolved in 450 mL dioxane and 450 mL 2N sodium hydroxide solution. The reaction mixture was refluxed for 2 h. Charcoal (1 g, Norit SA II) was added and reflux was continued for another 20 min. The mixture was filtered hot and washed with 50 mL 2N sodium hydroxide solution. The filtrate was treated with 550 mL 2N HCl and stirred at RT overnight. The solid material was filtered off and dried at 50° C. and 15 mbar. The desired compound was obtained as an off-white solid (28 g, 78%), MS: m/e=205.1 (M−H).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperaturereflux
  3. filtrationThe mixture was filtered hot
  4. washwashed with 50 mL 2N sodium hydroxide solution
  5. additionThe filtrate was treated with 550 mL 2N HCl
  6. filtrationThe solid material was filtered off
  7. customdried at 50° C.

Sources & evidence

ORD record
ord-4ae83a2595064a8898dd083b777a882f
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Reaction notes

Loading…