Benzyl Chloride → 3-Dibenzylaminophenoxyacetic acid methylester

HRID 414874Notes

Reaction equation

HRID 414874 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 10678961Methyl 2-(3-aminophenoxy)acetate

Product 1

HCID 866565173-Dibenzylaminophenoxyacetic acid methylester

Conditions

Temperature
100 °C

Procedure

10 g of 3-aminophenoxyacetic acid methylester are solved in 19 g benzyl chloride. Subsequently, 14 g of sodium carbonate are added portionwise and the temperature is raised to 100° C. The reaction mixture is stirred at this temperature for 3 hours. The insoluble salt is filtered off and washed with 100 ml of ethyl acetate. The combined filtrates are kept at 5° C. for 12 h. After the extraction with water and brine, the organic phase is dried with sodium sulfate and the solvent is removed in vacuum (50° C., 10−2 mbar). Yield: 22 g (dark oil).

Workup

  1. filtrationThe insoluble salt is filtered off
  2. washwashed with 100 ml of ethyl acetate
  3. waitThe combined filtrates are kept at 5° C. for 12 h
  4. extractionAfter the extraction with water and brine
  5. dry with materialthe organic phase is dried with sodium sulfate
  6. customthe solvent is removed in vacuum (50° C., 10−2 mbar)

Sources & evidence

ORD record
ord-d8f41782269540beb5e0c23e78fbed88
Source dataset
uspto-grants-2012_01
Patent number
US08088182B2

Reaction notes

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