Chloroacetyl chloride → N-(3-allyloxy-2-hydroxypropyl)-N-n-propyl-alpha-chloroacetamide
Reaction equation
[CH2:1]([O:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][CH2:9][CH2:10][CH3:11])[CH:2]=[CH2:3].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>C(Cl)Cl>[CH2:1]([O:4][CH2:5][CH:6]([OH:12])[CH2:7][N:8]([CH2:9][CH2:10][CH3:11])[C:22](=[O:23])[CH2:21][Cl:20])[CH:2]=[CH2:3]Participants
5
Procedure
A solution of 1-allyloxy-3-n-propylamino-2-propanol (95.2 g.) in a mixture of dry methylene chloride (275ml.) and triethylamine (80 ml.) is cooled to between -5° and 0°C. and a solution of chloroacetylchloride (42 ml.) in methylene chloride (60 ml.) is added dropwise with stirring during 2 hours. The mixture is allowed to warm to ambient temperature (18°-20°C.) and stirred at this temperature for 18 hours. The solution is washed with 2N hydrochloric acid (2 × 100 ml.) and then with water (100 ml.) and dried (MgSO4). Removal of the solvent under reduced pressure gives N-(3-allyloxy-2-hydroxypropyl)-N-n-propyl-α-cloroacetamide (119.7 g.) as an oil which is used without further purification.
Workup
- temperatureis cooled to between -5° and 0°C.
- stirringstirred at this temperature for 18 hours
- washThe solution is washed with 2N hydrochloric acid (2 × 100 ml.)
- dry with materialwith water (100 ml.) and dried (MgSO4)
- customRemoval of the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-f0cbc2e90bc1483caf9b926f621095b1
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03974156
Reaction notes
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