Ethanol → [3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Water	HCID 962	—
Reactant	Thionyl Chloride	HCID 24386	—
Reactant	9-(3-chlorophenyl)-alpha-(4-chlorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol	HCID 136096427	—
Solvent	Dichloromethane	HCID 6344	—
Product	[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone	HCID 17976096	17%

Reaction Steps

Thionyl chloride (0.1 ml) was added at room temperature to a mixture of compound 1 (0.0002 mol) in EtOH (2 ml). The mixture was stirred at room temperature for 2 hours. Water was added. The mixture was taken up in DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.15 g) was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH 98/2). The pure fractions were collected and the solvent was evaporated. The residue (0.03 g) was taken up in DCM and evaporated till dryness, yielding 0.023 g (17%) of compound 10.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07511138B2
Source dataset	uspto-grants-2009_03
ORD ID	ord-f0885ae53cdd40c0bc3e07fc5ec6fe31
Source note	uspto-grants-2009_03