Sodium hydride → 4-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-	HCID 10307909	—
Reactant	3-Benzoyloxy-4-chlorobenzyl bromide	HCID 16747840	—
Reactant	4-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole	HCID 21976891	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole	HCID 16749223	82.5%

Reaction Steps

The title compound was prepared by adapting the method for 4-[(3-benzyloxybenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole using NaH (60% dispersion in oil, 0.20 g, 5.0 mmol), 4-[(4-cyanophenyl)amino]-4H-[1,2,4]triazole (0.926 g, 5.0 mmol) and 3-benzoyloxy-4-chlorobenzyl bromide (1.63 g, 5.0 mmol) in anhydrous DMF (20 mL) to give 4-[(3-benzoyloxy-4-chlorobenzyl)(4-cyanophenyl)amino]-4H-[1,2,4]triazole as a white solid (1.773 g, 82%) after chromatography [SiO2, EtOAc (100%)]; δH (400 MHz, CDCl3) 4.93 (s, 2H), 6.66 (AA′BB′, 2H), 7.06 (dd, J=8.2, 2.0, 1H), 7.27 (d, J=2.0, 1H), 7.45 (d, J=8.2, 1H), 7.47-7.58 (m, 4H), 7.60-7.69 (m, 1H), 8.16-8.21 (m, 2H), 8.24 (s, 2H); LRMS (FAB+) m/z (rel. intensity) 430.1 (100, [M+H]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08148415B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-9f883cc93c6940bcaef90c5c65f21796
Source note	uspto-grants-2012_04