2,4-Difluorobenzaldehyde → N-(2,4-difluorobenzylidene)-N-[dimethyl(methoxymethyl)methyl]amine

HRID 636733Notes

Reaction equation

HRID 636733 reaction equation
Cl.[NH2:2][C:3]([CH3:8])([CH3:7])[CH2:4][O:5][CH3:6].[F:9][C:10]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:11]=1[CH:12]=O>C1(C)C=CC=CC=1>[F:9][C:10]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:11]=1[CH:12]=[N:2][C:3]([CH3:8])([CH3:7])[CH2:4][O:5][CH3:6]

Participants

4

Reactant 2

HCID 737702,4-DifluorobenzaldehydeHCID 212557121-Methoxy-2-methylpropan-2-amine hydrochloride

Product 1

HCID 21255697N-(2,4-difluorobenzylidene)-N-[dimethyl(methoxymethyl)methyl]amineYield 115.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the obtained 2-amino-2-methyl-1-methoxypropane hydrochloride (422 mg, 2.08 mmol) in toluene (7 ml) was added 2,4-difluorobenzaldehyde (310 mg, 2.18 mmol) and stirred under reflux using a Dean-Stark trap to remove water for 1 hour. Then triethylamine (1.0 ml) was added to the mixture and stirred for 6 hours. The precipitated hydrochloride was filtered off and the solvent was evaporated to give the crude title compound (547.5 mg).

Workup

  1. temperatureunder reflux
  2. customto remove water for 1 hour
  3. additionThen triethylamine (1.0 ml) was added to the mixture
  4. stirringstirred for 6 hours
  5. filtrationThe precipitated hydrochloride was filtered off
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6aa4f26bbaa240629fcbac19f4497f73
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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