Thionyl Chloride → 2-Chloro-5-benzoxazolecarbonitrile

https://huagongshe.com/reaction/1944697

Participants

Role	Name	HCID	Charge
Reactant	Thionyl Chloride	HCID 24386	—
Reactant	2-Thioxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile	HCID 10511479	—
Catalyst	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-Chloro-5-benzoxazolecarbonitrile	HCID 10631180	65%

Reaction Conditions

Temperature	67.5 °C

Reaction Steps

To a mixture of 2-thioxo-2,3-dihydrobenzooxazole-5-carbonitrile (2.56 g, 14.5 mmol) and thionylchloride (14.1 mL) was added two drops of DMF. The mixture was heated at 65-70° C. for 1 h. Then the mixture was cooled to rt and diluted with CH2Cl2. The solvent and excess thionylchloride were removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 20% EtOAc in Petroleum ether) to give 2-chlorobenzooxazole-5-carbonitrile 1.69 g (65%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08394842B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-b9fff86af60947f687d8d4689dc8ae3e
Source note	uspto-grants-2013_03