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>C(OCC)C>[Cl-:17].[CH:3](=[N+:2]([CH3:13])[CH3:1])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
10 g (56 mmol) of N,N,N′,N′-tetramethyl-C-phenylmethanediamine (J. Am. Chem. Soc. 77,1955, p. 1114–1116) were dissolved in 100 ml of diethyl ether and cooled to 0° C. in an ice-bath. 4.0 ml (56 mmol) of acetyl chloride were added dropwise under nitrogen. After the first drops, a white salt was precipitated, the temperature rose slightly. After 15 hours at room temperature, the supernatant liquor was decanted off and the solid was washed three times with 100 ml of diethyl ether each time, filtered over a protective gas frit under nitrogen and dried under an oil-pump vacuum until a constant weight was reached. In that manner, 7.7 g of benzylidenedimethylammonium chloride (corresponding to 81% of the theoretically calculated yield) were obtained.
Workup
- customAfter the first drops, a white salt was precipitated
- customthe supernatant liquor was decanted off
- washthe solid was washed three times with 100 ml of diethyl ether each time
- filtrationfiltered over a protective gas frit under nitrogen
- customdried under an oil-pump vacuum until a constant weight
Sources & evidence
- ORD record
- ord-157f30fae4cc4a4b9cc73c468c1132f8
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07012099B2
Reaction notes
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