[CH2:1]([NH:5][C:6](=[O:11])[O:7][CH2:8][C:9]#[CH:10])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].[I-:14].[Na+].ClCl>O.CO>[CH2:1]([NH:5][C:6](=[O:11])[O:7][CH2:8][C:9]#[C:10][I:14])[CH2:2][CH2:3][CH3:4]At 5° C., 19.0 g of propargyl butylcarbamate (0.122 mol), 12.2 g of sodium hydroxide (0.305 mol) and 18.5 g of sodium iodide (0.123 mol) are introduced as initial charge in 50 g of water and 48 g of methanol. Chlorine (11.7 g, 0.165 mmol) is then slowly introduced so that the temperature remains below 5° C. When the metered addition is complete, the mixture is stirred at this temperature for 1 h, then slowly heated to room temperature and stirred for 1 hour. After adding 100 g of water, the precipitated solid is isolated by filtration, washed with water and dried in vacuo. This gives 29.1 g of 3-iodo-2-propynyl N-butylcarbamate (purity: 94.7% (HPLC), polyiodized compounds: <0.1% (HPLC), yield: 80%).
Loading…
