Sodium Carbonate → Butenafine

HRID 620892

Reaction equation

HRID 620892 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:21]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[CH3:2][N:3]([CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)[CH2:29][C:28]1[CH:31]=[CH:32][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 16211748N-Methyl-N-naphthylmethylamine hydrochloride

Product 1

HCID 2484ButenafineYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-methyl-1-naphthylmethylamine hydrochloride (2.1 g; 0.01 mole) was dissolved in 50 ml of dry dimethylformamide, and 3.71 g (0.035 mole) of anhydrous sodium carbonate was added. The mixture was stirred at room temperature, and 2.49 g (0.011 mole) of p-t-butylbenzyl bromide was added. The mixture was reacted at 30° to 40° C. for 5 hours. Ice water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer was washed with water, and toluene was evaporated. The residue was chromatographed on a silica gel column, and eluted with 5% ethyl acetate/n-hexane. The eluate was concentrated to give 2.98 g (yield 94%) of an oily substance.

Workup

  1. customThe mixture was reacted at 30° to 40° C. for 5 hours
  2. extractionthe mixture was extracted with toluene
  3. washThe organic layer was washed with water, and toluene
  4. customwas evaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluted with 5% ethyl acetate/n-hexane
  7. concentrationThe eluate was concentrated
  8. customto give 2.98 g (yield 94%) of an oily substance

Sources & evidence

ORD record
ord-96d668be3870437ea6a038713631e2fa
Source dataset
uspto-grants-1989_04
Patent number
US04822822

Linked notes

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