Ethanolamine → 2-(benzyloxy)-N-(2-hydroxyethyl)benzamide

HRID 1698483Notes

Reaction equation

HRID 1698483 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]1([CH2:19][O:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23]([OH:25])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.[CH2:40]([CH2:42][NH2:43])[OH:41]>C1COCC1>[OH:41][CH2:40][CH2:42][NH:43][C:23]([C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[O:20][CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:25]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 18105812-Benzyloxybenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 566913072-(benzyloxy)-N-(2-hydroxyethyl)benzamideYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDAC) (1.3 g, 6.57 mmol) was slowly added to a solution of 2-(phenylmethoxy)benzoic acid (1.5 g, 6.57 mmol), 1-hydroxybenzotriazole (HOBt) (0.89 g, 6.57 mmol), and ethanolamine (0.40 mL, 6.57 mmol) in 50 mL of anhydrous THF at 0° C. The suspension was stirred and warmed up slowly to room temperature over 24 hrs. The reaction mixture was concentrated to dryness under reduced pressure and the resulting residue was diluted with dichloromethane and washed with 0.5N HCl twice followed by the addition of a saturated NaHCO3 solution and brine. The organic layer was separated, dried through a MgSO4 pad and concentrated under reduced pressure to afford 1.8 g (100%) of N-(2-Hydroxyethyl)[2-(phenylmethoxy)phenyl]carboxamide.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. additionthe resulting residue was diluted with dichloromethane
  3. washwashed with 0.5N HCl
  4. additiontwice followed by the addition of a saturated NaHCO3 solution and brine
  5. customThe organic layer was separated
  6. dry with materialdried through a MgSO4 pad
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a24dc6d4247345bcb29c01c3e2b11dbf
Source dataset
uspto-grants-2012_04
Patent number
US08163958B2

Reaction notes

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