N-Methyl-N-isopropylsulfamoyl amide

The Uses of N-Methyl-N-isopropylsulfamoyl amide

N-Isopropyl-N-methylsulfamide is an intermediate in the synthesis of unlabeled Saflufenacil-d7 (S081802). Saflufenacil-d7 is the labeled version of Saflufenacil (S081800), which is a herbicide of the pyrimidinedione chemical class used for the preplant burndown and selective preemergence dicot weed control in different field crops. It was found to inhibit protoporphyrinogen IX oxidase (PPO) enzyme.

Synthesis

Add 160g of ethanol to a 500ml four-necked flask, stir and cool to -5℃. Then, pass 18g (1.06mol) of ammonia gas, control the temperature at -5～0℃ and add 40g (0.23mol) of N-methyl-N-isopropylaminosulfonyl chloride at 0℃. After the addition is completed, keep warm for 1 hour, then control the vacuum of the reaction solution to -0.07MPa, the water bath temperature to 40℃, and concentrate under reduced pressure to dry solid. Add the solid to 120g of dichloromethane, stir at room temperature for 30 minutes to dissolve, and filter to obtain the filtrate. The filtrate is concentrated to dryness under reduced pressure at -0.07MPa and water bath temperature at 40℃ to obtain 33.7g of the product N-Methyl-N-isopropylsulfamoyl amide (HPLC purity 98.2%, yield 95%).