4-Aminobenzoic Acid → 4-amino-N-[2-(3-cyanophenoxy)ethyl]benzamide

HRID 747685Notes

Reaction equation

HRID 747685 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].C(N(CC)CC)C.[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.ON1C2C=CC=CC=2N=N1.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:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([NH2:21])=[CH:23][CH:24]=1)#[N:10]

Participants

7

Reactant 5

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226451983-(2-Aminoethoxy)benzonitrile hydrochloride

Product 1

HCID 177887164-amino-N-[2-(3-cyanophenoxy)ethyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.00 g (20.4 mmol) of 3-(2-aminoethoxy)benzonitrile hydrochloride was dissolved in 50 ml of dimethylformamide. 6.2 ml (43.8 mmol) of triethylamine, 2.00 g (14.6 mmol) of p-aminobenzoic acid, 1.98 g (14.6 mmol) of 1-hydroxybenzotriazole and 2.80 g (14.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to the solution at 0° C., and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner, the product was purified by the silica gel chromatography to obtain the title compound.

Workup

  1. customAfter the treatment with ethyl acetate as the extractant in an ordinary manner, the product was purified by the silica gel chromatography

Sources & evidence

ORD record
ord-d19843db5d8641669e638551c5e3cdd8
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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