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	US07655654B2
Source dataset	uspto-grants-2010_02
ORD ID	ord-9c750d7fc12f4319a8f5f5f4cf252d8e
Source note	uspto-grants-2010_02