Potassium Hydroxide → 4-Carboxy-2-fluoro-1-triphenylmethylimidazole

HRID 1463165Notes

Reaction equation

HRID 1463165 reaction equation
[CH:1]([C:3]1[N:4]=[C:5]([F:27])[N:6]([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1)=[O:2].[OH-:28].[K+]>C(O)C.C(Cl)Cl.O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([C:3]1[N:4]=[C:5]([F:27])[N:6]([C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1)([OH:28])=[O:2]

Participants

7

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 204324044-Carboxy-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 4

HCID 24470Silver NitrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-formyl-2-fluoro-1-triphenylmethylimidazole (356 mg.) in ethanol (5 ml.) and CH2Cl2 (3 ml.) was treated with silver nitrate (0.37 g.) in water (0.5 ml.) followed by the dropwise addition of 5 ml. of potassium hydroxide solution (5 ml. of a solution of 2.1 g. KOH in 35 ml. water). The mixture was stirred at room temperature for two hours, filtered and the filtrate extracted with ether. The aqueous layer was acidified with concentrated HCl and extracted with CHCl3. The organic layer was dried over MgSO4, filtered and the solvent evaporated to give 4-carboxy-2-fluoro-1-triphenylmethylimidazole (261 mg.) as a white solid having the following n.m.r. in d6DMSO: 7.0-7.68 (m, 16H); 11.5-12.5 (br, 1H).

Workup

  1. additionfollowed by the dropwise addition of 5 ml
  2. filtrationfiltered
  3. extractionthe filtrate extracted with ether
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-b33a6e474e9040cda81be9a0656cecae
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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