N-Methylpropylamine → 3,5-Bis(methyl-propylcarbamoyl)-benzoic acid ethyl ester

HRID 1436621Notes

Reaction equation

HRID 1436621 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](O)=[O:9])[CH:6]=1)[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.[CH3:33][N:34](C)[CH2:35][CH2:36][CH2:37]N=C=NCC.CNCCC>ClCCl>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[C:7]([C:8](=[O:9])[N:34]([CH3:33])[CH2:35][CH2:36][CH3:37])[CH:11]=[C:12]([C:14](=[O:20])[N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])[CH:13]=1)[CH3:2]

Participants

6

Reactant 4

HCID 12315N-MethylpropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 688146805-(Methyl-propylcarbamoyl)-isophthalic acid monoethyl ester

Product 1

HCID 688149203,5-Bis(methyl-propylcarbamoyl)-benzoic acid ethyl esterYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a solution of 5-(methyl-propylcarbamoyl)-isophthalic acid monoethyl ester (146 mg, 0.5 mmol), 1-hydroxybenzotriazole (68 mg, 0.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (96 mg, 0.5 mmol), N-methylpropylamine (51 μL, 0.5 mmol) in dichloromethane (2.5 mL) at room temperature overnight. Dilute with dichloromethane (15 mL) and wash with water (5 mL), 0.1 N 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, 90%)

Workup

  1. washwash with water (5 mL), 0.1 N 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-a8a90f5947ed434ea1b3909115b35176
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…