Ethylamine → 3-Ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acid ethyl ester

HRID 1436619Notes

Reaction equation

HRID 1436619 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:13]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:11]=[C:7]([C:8]([OH:10])=O)[CH:6]=1)[CH3:2].O[N:23]1[C:27]2C=CC=C[C:26]=2N=N1.C(N)C>CN(C=O)C.ClCCl>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:13]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:11]=[C:7]([C:8](=[O:10])[NH:23][CH2:27][CH3:26])[CH:6]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 688146805-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl ester

Product 1

HCID 688150393-Ethylcarbamoyl-5-(methyl-propylcarbamoyl)-benzoic acid ethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Stir a solution of 5-(methyl-propylcarbamoyl)-isophthalic acid monoethyl ester (146 mg, 0.5 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol), 1-(3-dimethylamninopropyl)-3-ethylcarbodiimide hydrochloride (110 mg, 0.55 mmol), ethylamine (2 N in THF, 0.275 mL, 0.55 mmol) in 0.75 mL DMF at room temperature overnight. Dilute with dichloromethane (15 mL) and wash with water (5 mL), 0.1 N aqueous citric acid (5 mL), saturated aqueous sodium bicarbonate (5 mL), and saturated aqueous sodium chloride (5 mL). Dry (magnesium sulfate) and concentrate to give the title compound (157 mg, 100%).

Workup

  1. washwash with water (5 mL), 0.1 N aqueous citric acid (5 mL), saturated aqueous sodium bicarbonate (5 mL), and saturated aqueous sodium chloride (5 mL)
  2. dry with materialDry (magnesium sulfate)
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-f8acb160258b4707a86e0aaac26142c5
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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