Pyridine → 2-Fluoro-4-hydroxyiminomethyl-1-triphenylmethylimidazole

HRID 2412474Notes

Reaction equation

HRID 2412474 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.Cl.[NH2:29][OH:30].N1C=CC=CC=1>C(O)C>[F:27][C:5]1[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]=[C:3]([CH:1]=[N:29][OH:30])[N:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 537790282-Fluoro-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 571816302-Fluoro-4-hydroxyiminomethyl-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 4-formyl-2-fluoro-1-triphenylmethylimidazole (0.356 g.) and hydroxylamine hydrochloride (0.035 g.) in ethanol (4 ml.) was added pyridine (0.2 ml.). Stirring was continued at ambient temperature for 18 hours and the precipitated solid was filtered to give 2-fluoro-4-hydroxyiminomethyl-1-triphenylmethylimidazole, m.p. 147°-149°. Further amounts of product could be isolated from the mother liquors.

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-e9a3cbc06be849fb8b04009829676831
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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