Diethyl Ether → HCID 23338377, compound

HRID 28036Notes

Reaction equation

HRID 28036 reaction equation
[CH3:1][CH:2]1[CH:6]([CH3:7])[O:5][CH:4]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2OCC)[O:3]1.[CH2:19]([O:21][CH2:22]C)[CH3:20].[C:24](=[O:27])([O-])[O-].[Na+].[Na+].[Cl:30]CC(Cl)=O>O>[CH3:7][CH:6]1[CH:2]([CH3:1])[O:3][CH:4]([CH2:8][N:9]([C:24](=[O:27])[CH:22]([O:21][CH2:19][CH3:20])[Cl:30])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 23338375HCID 23338375, compound

Product 1

HCID 23338377HCID 23338377, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(4,5-Dimethyl-1,3-dioxolan-2-ylmethyl)-2-ethoxyaniline (5.41 ml; 0.022 mole), diethyl ether (30 ml), sodium carbonate (4.66 grams) and water (50 ml) were charged into a glass reaction vessel equipped with stirrer, thermometer and cooling means. The mixture was cooled to a temperature of 4° to 6° C. and chloroacetyl chloride (2.71 ml) was slowly added with stirring. After the addition was completed stirring was continued for a period of 1 hour. After this time the organic phase was separated from the aqueous phase and filtered. The filtrate was then washed with aqueous sodium carbonate and thereafter dried over anhydrous magnesium sulfate. The dried solution was filtered and stripped of solvent under reduced pressure to yield the desired product N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-ethoxy-α-chloroacetanilide as a white solid having a melt point of 43.0° C.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and cooling means
  3. additionwas slowly added
  4. additionAfter the addition
  5. stirringwas completed stirring
  6. customAfter this time the organic phase was separated from the aqueous phase
  7. filtrationfiltered
  8. washThe filtrate was then washed with aqueous sodium carbonate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe dried solution was filtered

Sources & evidence

ORD record
ord-8ba8670235d44cfd80ed48d219ac36d8
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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