Diethyl Ether → HCID 23338384, compound

HRID 28038Notes

Reaction equation

HRID 28038 reaction equation
[CH2:1]([CH:3]1[CH2:7][O:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2OC)[O:4]1)[CH3:2].[CH2:18]([O:20][CH2:21]C)C.[C:23](=[O:26])([O-])[O-].[Na+].[Na+].[Cl:29]CC(Cl)=O>O>[CH2:1]([CH:3]1[CH2:7][O:6][CH:5]([CH2:8][N:9]([C:23](=[O:26])[CH:18]([O:20][CH3:21])[Cl:29])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 23338373HCID 23338373, compound

Product 1

HCID 23338384HCID 23338384, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

N-(4-Ethyl-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-ethyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-α-chloroacetanilide as the residue.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and cooling means
  3. additionAfter the addition
  4. stirringstirring
  5. customAfter this time the organic phase is separated from the aqueous phase
  6. filtrationis filtered
  7. washThe filtrate is then washed with aqueous sodium carbonate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-7b2e02b4e6a24ab6aa97f6d1fa8b5da3
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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