Thionyl Chloride → HCID 89545295, compound

Participants

Reaction Conditions

Reaction Steps

500 mg (1.56 mmol) of 2-chloro-4-(methylsulfonyl)-3-{[(propan-2-ylideneamino)oxy]methyl}benzoic acid and 395 mg (1.34 mmol) of 1-methyl-1H-1,2,4-triazole-5-amine were dissolved in 2.5 ml of pyridine, and 10 mg of 4-dimethylaminopyridine and a drop of DMF were added. At RT, 313 mg (2.58 mmol) of thionyl chloride were then added dropwise, and the mixture was stirred at 70° C. for 5 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 on a silica gel column. Yield: 153 mg (24%) as a colorless oil.

Provenance & Evidence