Iodine → 3-Iodo-2-propynyl butylcarbamate

Participants

Reaction Steps

At 8° C., 10.1 g of sodium hydroxide (0.244 mol) and 19.0 g of propargyl butylcarbamate (0.122 mol) are introduced as initial charge in 48 g of methanol and 50 g of water. At this temperature, 15.5 g of iodine (0.061 mol) are added in portions. Chlorine (5.6 g, 0.079 mol) is then slowly introduced into the reaction mixture so that the temperature still remains below 8° C. When the metered addition is complete, the mixture is stirred for 1 h at this temperature and then 105 g of water are added. The precipitated solid is isolated by filtration, washed with water and dried in vacuo. This gives 28.5 g of 3-iodo-2-propynyl N-butylcarbamate (purity: 95.0% (HPLC), polyiodized compounds: 0.3% (HPLC), yield: 79%).

Provenance & Evidence