Diethyl Ether → N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-alpha-chloroacetanilide

HRID 28035Notes

Reaction equation

HRID 28035 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]=2OC)[O:3]1.[CH2:18]([O:20][CH2:21]C)C.[C:23](=[O:26])([O-])[O-].[Na+].[Na+].[Cl:29]CC(Cl)=O>O>[CH3:7][CH:6]1[CH:2]([CH3:1])[O:3][CH:4]([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:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 23338386N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline

Product 1

HCID 23338385N-(4,5-dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxy-alpha-chloroacetanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(4,5-Dimethyl-1,3-dioxolan-2-ylmethyl)-2-methoxyaniline (5.21 grams), diethyl ether (30 ml), sodium carbonate (4.66 grams) and water (50 ml) were charged into a glass reaction flask equipped with stirrer, thermometer and cooling means. The mixture was cooled to a temperature of 0° to 5° C. and chloroacetyl chloride (2 ml) was slowly added with stirring. After the addition was completed, the mixture was stirred for a period of 1 hour. After this time the organic phase was separated from the aqueous phase and filtered. The filtrate was washed with aqueous sodium carbonate three times and then 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-methoxy-α-chloroacetanilide as a white crystalline solid having a melt point of 72° to 73° C.

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 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 three times
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe dried solution was filtered

Sources & evidence

ORD record
ord-22d7af3315464ac2ad3e98033d5ddb0c
Source dataset
uspto-grants-1980_09
Patent number
US04225335

Reaction notes

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