Ethoxyacetic acid → N-benzyl-2-ethoxy-N-ethylacetamide

HRID 1391771Notes

Reaction equation

HRID 1391771 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][CH2:16][C:17]([OH:19])=O)[CH3:14].[CH2:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21]>C(Cl)Cl>[CH2:20]([N:22]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:17](=[O:19])[CH2:16][O:15][CH2:13][CH3:14])[CH3:21]

Participants

5

Reactant 3

HCID 12301Ethoxyacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 84352N-Ethylbenzylamine

Product 1

HCID 2162886N-benzyl-2-ethoxy-N-ethylacetamideYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of 1,1′-carbonyldiimidazole (4.68 g, 28.86 mmol) in dry DCM (15 mL) was added portion-wise over 15 min to a solution of ethoxyacetic acid (2.09 mL, 22.12 mmol) in DCM (30 mL) under nitrogen at room temperature. The resulting solution was stirred under nitrogen for 1 h and then treated with a solution of N-ethylbenzylamine (6.60 mL, 44.37 mol) in dry dichloromethane (30 mL) drop-wise over 15 min. The resultant solution was stirred under nitrogen at room temperature for 18 h and then partitioned with aqueous HCl (2M, 2×75 mL) and the combined organic layer dried (MgSO4), filtered and reduced in vacuo to give an oil. Purification by SPE (silica, 2×50 g cartridges), eluting with cyclohexane:EtOAc gradient 15:1 to 1:1 afforded the title compound as a pale yellow oil (4.36 g).

Workup

  1. custompartitioned with aqueous HCl (2M, 2×75 mL)
  2. dry with materialthe combined organic layer dried (MgSO4)
  3. filtrationfiltered
  4. customto give an oil
  5. customPurification by SPE (silica, 2×50 g cartridges)
  6. washeluting with cyclohexane

Sources & evidence

ORD record
ord-e5c676dcaa7a4ecd916f2079fdb2d4f7
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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