Chloroacetyl chloride → 2-Chloro-N-(2-ethoxy-2-oxoethyl)ethanimidic acid
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C([O-])(O)=O.[Na+].[Cl:14][CH2:15][C:16](Cl)=[O:17]>>[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH:7][C:16](=[O:17])[CH2:15][Cl:14])[CH3:3]Participants
4
Procedure
Twenty-seven and nine-tenths grams (g) (0.2 mole) of glycine ethyl ester --HCl was combined with about 100 grams of ice in a reaction flask. Solid NaHCO3 (33.6 g) (0.4 mole) was then added to this mixture followed by dropwise addition of 23.0 g (0.2 mole) of chloroacetyl chloride with stirring. The temperature of the reaction mixture was maintained between -10° and -5° C. by ice addition. The solid precipitate that formed was separated from the reaction mixture by filtration, washed with ice water and air dried. The yield was 15 g (41.7%) of a solid having a melting point of 60°-62° C. which was identified as the title compound by infrared (IR) spectroscopy analysis.
Workup
- temperatureThe temperature of the reaction mixture was maintained between -10° and -5° C. by ice addition
- customThe solid precipitate that formed
- customwas separated from the reaction mixture by filtration
- washwashed with ice water and air
- customdried
Sources & evidence
- ORD record
- ord-06a170dc25aa497e939c5e8396ab7657
- Source dataset
- uspto-grants-1982_11
- Patent number
- US04361439
Reaction notes
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