Butyl iodide → HCID 178448490, compound

Participants

Role	Name	HCID	Charge
Reactant	Butyl iodide	HCID 10962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide	HCID 87094486	—
Catalyst	Tetraethylammonium Iodide	HCID 6225	—
Catalyst	Tetrabutylammonium Iodide	HCID 67553	—
Catalyst	Tetrabutylammonium hydrogen sulfate	HCID 94433	—
Solvent	Toluene	HCID 1140	—
Product	HCID 178448490	HCID 178448490	85.3%

Reaction Steps

A mixture of Example 2C (650 mg, 2 mmol), 1-iodobutane (920 mg, 5 mmol), potassium carbonate (653 mg, 4 mmol), tetrabutylammonium iodide (20 mg, 0.05 mmol), tetrabutylammonium hydrogensulfate (20 mg, 0.06 mmol) and tetraethylammonium iodide (20 mg, 0.07 mmol) in anhydrous toluene (60 mL) was refluxed for 15 h. The mixture was then washed with water, brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was chromatographed over silica gel (EtOAc-Hexane 1:1) to afford 650 mg of the title compound. MS (DCI/NH3) m/z 381 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08895592B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-d3d60ed4735e4fb49b32cad7e2b5cd0a
Source note	uspto-grants-2014_11