Oxalyl chloride → HCID 89545072, compound

Participants

Reaction Conditions

Reaction Steps

400 mg (1.61 mmol) of 2,4-dichloro-3-[(methoxyimino)methyl]benzoic acid and 228 mg (2.0 mmol) of 5-ethyl-1,3,4-oxadiazole-2-amine were dissolved in 3 ml of pyridine, and 10 mg of 4-dimethylaminopyridine and a drop of DMF were added. At room temperature (RT), 255.83 mg (2.016 mmol) of oxalyl chloride were then added dropwise, and the mixture was stirred at 70° C. for 4 h. 0.5 ml of water was then added to the reaction, which had once more been cooled, and the mixture was stirred for about 30 min, acidified with a saturated KHSO4 solution and extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases were washed once with 20 ml of a saturated NaHCO3 solution, dried over MgSO4, filtered off and concentrated. The residue was purified chromatographically by preparative HPLC. Yield: 99.3 mg (18%) as colorless crystals.

Provenance & Evidence