Cesium carbonate → N-(benzhydrylideneamino)-2-[(E)-(benzhydrylidenehydrazinylidene)methyl]thiophen-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Diphenylmethylidenehydrazine	HCID 79304	—
Reactant	(E)-N-[(E)-(3-bromothiophen-2-yl)methylideneamino]-1,1-diphenylmethanimine	HCID 89330312	—
Catalyst	palladium(II) acetate	HCID 167845	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Solvent	Toluene	HCID 1140	—
Product	N-(benzhydrylideneamino)-2-[(E)-(benzhydrylidenehydrazinylidene)methyl]thiophen-3-amine	HCID 89330308	79%

Reaction Conditions

Temperature	85 °C

Reaction Steps

To a mixture of (E)-1-((3-bromothiophen-2-yl)methylene)-2-(diphenylmethylene)hydrazine (15 g, 40.6 mmol, including its Z isomer) and (diphenylmethylene)hydrazine (9.57 g, 48.7 mmol) in toluene (125 mL) was added palladium(II) acetate (0.120 g, 2.031 mmol), 1,1′-bis(diphenylphosphino)ferrocene (2.252 g, 4.06 mmol) and Cs2CO3 (26.5 g, 81 mmol). The reaction mixture was stirred at 85° C. for 14 hours and was subsequently diluted with toluene (25 mL) and filtered to remove undissolved solids. The filtrate was purified by flash column chromatography. The pure product fractions were evaporated to give the title compound (15.5 g, 79%). ESI-MS m/z [M+H]+ calc'd for C31H24N4S, 485. found, 485.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09056873B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-99fcdd3a670c4a1eb20e558b7eb908b8
Source note	uspto-grants-2015_06