Water → HCID 59497645, compound

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	1,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one	HCID 100278	—
Reactant	3-(Bromomethyl)-5-chloro-1-benzothiophene	HCID 2779857	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 59497645	HCID 59497645	87%

Reaction Steps

To a solution of 1-isopropenylbenzimidazolone (0.3 g, 1.72 mmol) in DMF (5 mL) was added 60% NaH (0.1 g, 2.6 mmol). The reaction mixture was stirred at room temperature for 15 min and added 3-(Bromomethyl)-5-chlorobenzo[b]thiophene (0.54 g, 2.07 mmol). The reaction mixture was heated to 65° C. and stirred at that temperature for 2 h. When the reaction was complete, the mixture was treated with water. The mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC to afford 0.53 g (87%) of the desired product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09150556B2
Source dataset	uspto-grants-2015_10
ORD ID	ord-e136429283894ac6a9925b20afc9f07e
Source note	uspto-grants-2015_10