Sodium Hydroxide → HCID 178474043, compound

HRID 480478Notes

Reaction equation

HRID 480478 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:54]([O-:57])(=O)[CH3:55].[Na+].Cl.NO.[OH-].[Na+]>C1COCC1.CO>[OH:29][C:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([NH:14][C:54](=[O:57])[CH3:55])[CH:24]=[CH:23]2)([C:30]1[N:31]=[CH:32][NH:33][CH:34]=1)[CH:26]([CH3:27])[CH3:28]

Participants

7

Reactant 4

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

Product 1

HCID 178474043HCID 178474043, compoundYield 164.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-{6-[(diphenylmethylene)amino]naphthalene-2-yl}-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (15.0 g) in THF (100 mL)-methanol (100 mL) were added sodium acetate (4.29 g) and hydroxylamine hydrochloride (2.73 g), and the mixture was stirred at room temperature for 20 min. After addition of 0.1N-NaOH solution, the mixture was extracted with ethyl acetate. The extract was washed with brine, dried and concentrated. The residue was dissolved in dichloromethane and pyridine (5.3 mL) and acetic anhydride (4.1 mL) were added. The mixture was stirred at room temperature for 40 min and then saturated sodium bicarbonate solution was added and was extracted with dichloromethane. The extract was dried and concentrated and the residue was crystallized from ethyl acetate to give the titled compound (11.6 g) as pale red crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. additionpyridine (5.3 mL) and acetic anhydride (4.1 mL) were added
  7. stirringThe mixture was stirred at room temperature for 40 min
  8. additionsaturated sodium bicarbonate solution was added
  9. extractionwas extracted with dichloromethane
  10. customThe extract was dried
  11. concentrationconcentrated
  12. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-64ac674b98ee4fe693bb4fd5b9eb7c72
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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