N,N'-Dimethylethylenediamine → ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Sodium Azide	HCID 33557	—
Reactant	1-Ethyl-4-ethynylbenzene	HCID 142425	—
Reactant	Ethyl 3-iodobenzoate	HCID 143542	—
Reactant	Sodium Ascorbate	HCID 23667548	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	(Methanesulfinyl)methane--water (1/1)	HCID 23503278	—
Product	ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate	HCID 67030215	—

Reaction Steps

A mixture of ethyl 3-iodobenzoate (4-1) (138 mg, 0.5 mmol), sodium azide (34 mg, 0.52 mmol), 1-ethyl-4-ethynylbenzene (4-2) (65 mg, 0.5 mmol), CuI (10 mg), MeNHCH2CH2NHMe (11 μL), sodium ascorbate (10 mg), DMSO-H2O (v/v 5:1, 1.5 mL) is stirred at room temperature for 2 hours. The reaction mixture is then poured into ethyl acetate (50 mL), washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and evaporated. The residue is purified on silica gel (0-33% ethyl acetate in hexane) to give ethyl 3-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]benzoate as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08362050B2
Source dataset	uspto-grants-2013_01
ORD ID	ord-04d8a6fc35784539b2a7b23ce7e955f3
Source note	uspto-grants-2013_01