Diethyl Ether → N-alpha-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-ethyl-6-methylaniline
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16].C(=O)([O-])[O-].[Na+].[Na+].CCOCC.[Cl:28][CH2:29][C:30](Cl)=[O:31]>O>[Cl:28][CH2:29][C:30]([N:7]([CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH3:16])=[O:31]Participants
6
Procedure
N-(1,3-Dioxolan-2-ylmethyl)-2-ethyl-6-methylaniline (7.5 grams), sodium carbonate (5.0 grams), ether (100 ml) and water (40 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and thermometer. The mixture was cooled to a temperature of about 0° C. and chloroacetyl chloride (4.5 grams) was added, with stirring, over a period of about 15 minutes. After the addition was completed stirring was continued for a period of about one hour. After this time the resulting solution was washed with water and the washed solution was dried over anhydrous magnesium sulfate and stripped of solvent under reduced pressure to yield the desired product N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-ethyl-6-methylaniline.
Workup
- customequipped with a mechanical stirrer
- additionwas added
- additionAfter the addition
- stirringwas completed stirring
- waitwas continued for a period of about one hour
- washAfter this time the resulting solution was washed with water
- dry with materialthe washed solution was dried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-33854370f07b43d28c8b2dad38b0c96b
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04022608
Reaction notes
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