Acetyl chloride → Methanaminium, N-methyl-N-(phenylmethylene)-, chloride
Reaction equation
[CH3:1][N:2]([CH3:13])[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)N(C)C.C([Cl:17])(=O)C>CCOCC>[Cl-:17].[CH:3](=[N+:2]([CH3:13])[CH3:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
10 g (56 mmole) of N,N,N′, N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77 (1955) 1114-1116) were dissolved in 100 ml ether and the solution was cooled to 0° C. in an ice-bath. 4.0 ml (56 mmole) acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt precipitated out and the temperature increased slightly. After 15 hours at RT, the mixture was decanted and the solid was washed three times with 100 ml ether each time, filtered over an inert gas frit under nitrogen and dried to constant weight under an oil-pump vacuum. 7.7 g benzylidenedimethylammonium chloride (80.9% of theoretical) were obtained in this manner.
Workup
- customAfter the first drops, a white salt precipitated out
- temperaturethe temperature increased slightly
- customthe mixture was decanted
- washthe solid was washed three times with 100 ml ether each time
- filtrationfiltered over an inert gas frit under nitrogen
- customdried to constant weight under an oil-pump vacuum
Sources & evidence
- ORD record
- ord-63b84bfb6b284844b53239d4430549b7
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288278B1
Reaction notes
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