Sodium Hydroxide → HCID 178450079, compound

HRID 1368553Notes

Reaction equation

HRID 1368553 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([C:25]([C:30]2[N:31]=[CH:32][N:33](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:34]=2)([OH:29])[CH:26]([CH3:28])[CH3:27])[CH:19]=[CH:18]3)C2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Na+].Cl.NO.[OH-].[Na+]>C1COCC1.CO>[NH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([C:25]([C:30]1[N:31]=[CH:32][NH:33][CH:34]=1)([OH:29])[CH:26]([CH3:28])[CH3:27])[CH:19]=[CH:18]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 22018326HCID 22018326, compound

Product 1

HCID 178450079HCID 178450079, compoundYield 176%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-{6-[(Diphenylmethylene)amino]naphthalen-2-yl}-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (1.0 g) was dissolved in THF (5 ml)-methanol (5 ml). To the solution were added sodium acetate (285 mg) and hydroxylamine hydrochloride (181 mg), and the mixture was stirred at room temperature for 20 min. To the mixture was added 0.1N-aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution and dried. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=2:1→1:1) to give the titled compound (720 mg) as a pale red powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-e17d77986f6843d699dd1a551f75dcbe
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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