Water → N-(4-methyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-alpha-chloroacetamide

HRID 28046Notes

Reaction equation

HRID 28046 reaction equation
[CH3:1][CH:2]1[CH2:6][O:5][CH:4]([CH2:7][NH:8]C2C=CC=CC=2OC)O1.[CH2:17]([O:19][CH2:20]C)C.[C:22](=[O:25])([O-])[O-].[Na+].[Na+].[Cl:28]CC(Cl)=O.[OH2:33]>>[CH3:1][CH:2]1[CH2:6][O:5][CH:4]([CH2:7][NH:8][C:22](=[O:25])[CH:17]([O:19][CH3:20])[Cl:28])[O:33]1

Participants

6

Procedure

N-(4-Methyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline (0.02 mole), diethyl ether (50 ml), sodium carbonate (4.66 grams) and water (30 ml) were charged into a glass reaction vessel equipped with stirrer, thermometer and cooling means. The mixture was cooled to a temperature of 0° to 5° C. and chloroacetyl chloride (0.22 moles) was slowly added with stirring. After the addition was completed, the mixture was stirred for a period of about 1 hour. After this time the organic phase was separated from the aqueous phase and filtered. The filtrate was washed with aqueous sodium carbonate and dried over anhydrous magnesium sulfate. The dried solution was filtered and stripped of solvent under reduced pressure to yield the desired product N-(4-methyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-α-chloroacetamide.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and cooling means
  3. additionwas slowly added
  4. additionAfter the addition
  5. stirringthe mixture was stirred for a period of about 1 hour
  6. customAfter this time the organic phase was separated from the aqueous phase
  7. filtrationfiltered
  8. washThe filtrate was washed with aqueous sodium carbonate
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe dried solution was filtered

Sources & evidence

ORD record
ord-e937ad8ec1cb43328776cd4463a323cc
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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