Bromobenzene → 8-Chloro-1-phenyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

Participants

Role	Name	HCID	Charge
Reactant	Bromobenzene	HCID 7961	—
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	HCID 11390173	HCID 11390173	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Product	8-Chloro-1-phenyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione	HCID 66934680	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

8-Chloro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (iv-j) (500 mg, 2.4 mmol) was combined with K2CO3 (660 mg, 4.8 mmol) under an atmosphere of argon. Phenylbromide (370 mg, 2.4 mmol) and N,N′-Dimethyl-ethane-1,2-diamine (21 mg, 0.24 mmol, 10 mol %) were added, followed by 10 mL of toluene. The mixture was degassed with an argon sparge for 10 min. CuI (23 mg, 0.12 mmol, 5 mol %) was added and the reaction was heated to 110° C. for 48 h. The mixture was filtered and volatiles removed in vacuo. Chromatographic purification provided the desired product contaminated with 10% 8-chloro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (172 mg, 34%) MS m/z=286 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07935694B2
Source dataset	uspto-grants-2011_05
ORD ID	ord-df4f8aa047494557a217d04cccc12fd6
Source note	uspto-grants-2011_05