Diethyl Ether → N-(4-propyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-alpha-chloroacetanilide

HRID 28040Notes

Reaction equation

[CH2:1]([CH:4]1[CH2:8][O:7][CH:6]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2OC)[O:5]1)[CH2:2][CH3:3].[CH2:19]([O:21][CH2:22]C)C.[C:24](=[O:27])([O-])[O-].[Na+].[Na+].[Cl:30]CC(Cl)=O>O>[CH2:1]([CH:4]1[CH2:8][O:7][CH:6]([CH2:9][N:10]([C:24](=[O:27])[CH:19]([O:21][CH3:22])[Cl:30])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:5]1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

N-(4-Propyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline (0.25 mole), diethyl ether (30 ml), sodium carbonate (35.5 grams) and water (50 ml) are charged into a glass reaction vessel equipped with stirrer, thermometer and cooling means. The mixture is cooled to about 5° C. and chloroacetyl chloride (0.28 mole) is added dropwise with stirring. After the addition is completed, stirring is continued for 1 hour. After this time the organic phase is separated from the aqueous phase and is filtered. The filtrate is then washed with aqueous sodium carbonate, dried over anhydrous magnesium sulfate and filtered. The filtrate is then stripped of solvent under reduced pressure to yield the desired product N-(4-propyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-α-chloroacetanilide as the residue.

Workup

customequipped with stirrer
temperaturethermometer and cooling means
additionAfter the addition
stirringstirring
customAfter this time the organic phase is separated from the aqueous phase
filtrationis filtered
washThe filtrate is then washed with aqueous sodium carbonate
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered

Sources & evidence

ORD record: ord-014ae2fa5ffd4701817a05d6204d0400
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04225335

Reaction notes

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