Benzene → N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-alpha-bromopropionamide
Reaction equation
[CH3:1][C:2]([NH:6][CH2:7][CH:8]1[O:12][CH:11]([CH3:13])[CH:10]([CH3:14])[O:9]1)([CH3:5])[C:3]#[CH:4].C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:27][CH:28]([CH3:32])[C:29](Cl)=[O:30]>O>[CH3:5][C:2]([N:6]([CH2:7][CH:8]1[O:9][CH:10]([CH3:14])[CH:11]([CH3:13])[O:12]1)[C:29](=[O:30])[CH:28]([Br:27])[CH3:32])([CH3:1])[C:3]#[CH:4]Participants
Procedure
N-(1,1-Dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)amine (10 grams), benzene (100 ml), water (100 ml) and sodium carbonate (8 grams) are charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The reaction mixture is cooled to a temperature of 5° to 10° C. and α-bromopropionyl chloride (7 grams) is added dropwise with stirring. After the addition is completed stirring is continued until the reaction mixture reaches room temperature. After this time the organic phase is separated from the aqueous phase and is washed with water. The washed solution is then dried over anhydrous magnesium sulfate, filtered and stripped of solvent under reduced pressure to yield the desired product N-(1,1-dimethylprop-2-ynyl)-N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-α-bromopropionamide.
Workup
- customequipped with a mechanical stirrer
- additionis added dropwise
- additionAfter the addition
- stirringis completed stirring
- customreaches room temperature
- customAfter this time the organic phase is separated from the aqueous phase
- washis washed with water
- dry with materialThe washed solution is then dried over anhydrous magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-8fd29abf78944d6b87ed31d10ffd5cbf
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04113464
Reaction notes
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