Triethylamine → N-[2-(3-cyanophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamide

HRID 2187960Notes

Reaction equation

HRID 2187960 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)=[O:20].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[C:9]([C:8]1[CH:7]=[C:6]([CH:13]=[CH:12][CH:11]=1)[O:5][CH2:4][CH2:3][NH:2][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([C:19](=[O:20])[C:18]2[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:16]([O:15][CH3:14])[CH:17]=2)=[CH:22][CH:23]=1)#[N:10]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226451983-(2-Aminoethoxy)benzonitrile hydrochlorideHCID 226452014-(3,4-Dimethoxybenzoyl)benzoic acid

Product 1

HCID 22645151N-[2-(3-cyanophenoxy)ethyl]-4-(3,4-dimethoxybenzoyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.68 g (3.45 mmol) of 3-(2-aminoethoxy)benzonitrile monohydrochloride was dissolved in 20 ml of N,N-dimethylformamide (dehydrated). 0.9 g (3.14 mmol) of 4-(3,4-dimethoxybenzoyl)benzoic acid, 0.47 g (3.45 mmol) of 1-hydroxybenzotriazole, 0.48 ml (3.45 mmol) of triethylamine and 0.66 g (3.45 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to the obtained solution, and they were stirred overnight. The solvent was evaporated, and the residue was treated with ethyl acetate as the extraction solvent in an ordinary manner to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with ethyl acetate as the extraction solvent in an ordinary manner

Sources & evidence

ORD record
ord-050476c3305948d3acb32b3dd289b06a
Source dataset
uspto-grants-2002_06
Patent number
US06410538B2

Reaction notes

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