Dimethylformamide → HCID 22933011, compound

To a solution of 4-iodo-2,6-dimethoxybenzoic acid (603.0 mg, 1.96 mmol), synthesized by the process described in Reference Example 11, in methylene chloride (12 mL) were added dimethylformamide (0.020 mL, 0.26 mmol) and oxalyl chloride (0.26 mL, 3.0 mmol). After stirring at room temperature for 30 minutes, the resulting solution was poured into an ice-cold solution of triethylamine (0.50 mL, 3.6 mmol) in ethanol (10 mL). The reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. A solution of the residue in diethyl ether was washed successively with water, 0.1 M hydrochloric acid and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield the title compound as a colorless oil (641.0 mg, yield: 97%).

1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
2. concentrationconcentrated under reduced pressure
3. washA solution of the residue in diethyl ether was washed successively with water, 0.1 M hydrochloric acid and brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel

ORD record

ord-e999ab154b054a42b05966bef63db8a0

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06706703B2