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 of ether and cooled to 0° C. in an ice bath. 4.0 ml (56 mmole) of acetyl chloride were added under nitrogen. After the first few drops a white salt precipitated out and the temperature rose slightly. After 15 hours at RT the liquid was decanted off and the solids were washed three times, each time with 100 ml of ether, filtered under nitrogen through a protective gas frit, and dried to constant weight in an oil pump vacuum. 7.7 g of benzylidene dimethyl ammonium chloride (80.9% of theory) were obtained in this way.
Workup
- customAfter the first few drops a white salt precipitated out
- customAfter 15 hours at RT the liquid was decanted off
- washthe solids were washed three times
- filtrationeach time with 100 ml of ether, filtered under nitrogen through a protective gas frit
- customdried to constant weight in an oil pump vacuum
Sources & evidence
- ORD record
- ord-09369142d5b449a9bea50af73321f713
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410790B1
Reaction notes
Loading…