Methyl chloroacetate → HCID 20458559, compound
Reaction equation
[CH2:1]([N:4]([CH2:6][CH:7]=[CH2:8])[CH3:5])[CH:2]=[CH2:3].[Cl:9][CH2:10][C:11]([O:13][CH3:14])=[O:12]>CC(C)=O>[Cl-:9].[C:11]([CH2:10][N+:4]([CH3:5])([CH2:6][CH:7]=[CH2:8])[CH2:1][CH:2]=[CH2:3])([O:13][CH3:14])=[O:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diallyl methylamine (17.90 g) in acetone (35 ml) was added methyl chloracetate (17.47 g). The mixture was allowed to stand at ambient temperature for 48 hours. The solvent was then removed by evaporation under reduced pressure. The residue, a thick oil, was made more mobile by the addition of isopropanol (5.0 ml) and the product re-precipitated by the addition of ether (700 ml). The product separated as a heavy oil. The ether layer was decanted and the product again mobilised by the addition of isopropanol (5.0 ml). Any residual ether and the isopropanol were removed by evaporation under a vacuum of 1 mmHg and gentle heating. The product N-carbomethoxy methyl-N-methyl-N,N-diallyl ammonium chloride (29.20 g) was isolated as a pale yellow oil (free from starting materials by glc).
Workup
- customThe solvent was then removed by evaporation under reduced pressure
- additionThe residue, a thick oil, was made more mobile by the addition of isopropanol (5.0 ml)
- customthe product re-precipitated by the addition of ether (700 ml)
- customThe product separated as a heavy oil
- customThe ether layer was decanted
- additionthe product again mobilised by the addition of isopropanol (5.0 ml)
- customAny residual ether and the isopropanol were removed by evaporation under a vacuum of 1 mmHg and gentle heating
Sources & evidence
- ORD record
- ord-2d0e9bc1adc74dcc8c8f99a221d98c0c
- Source dataset
- uspto-grants-1984_05
- Patent number
- US04451624
Reaction notes
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