Water → HCID 11486936, compound

Participants

Reaction Steps

To a nitrogen purged 2 L three necked flask equipped with addition funnel, overhead stirrer and reflux condenser was charged 150 g(0.591 mol) 4-Chloro-2-iodo-phenylamine, 3 g(0.018 mol, 0.03 eq) benzenesulfonic acid and 500 mL acetontrile. The mixture was warmed to 70 C and 120 g (0.652 mol, 1.1 eq) benzhydrol dissolved in 500 mL acetonitrile was added to the stirred warm solution over a period of 7.5 h. After another 4 h, LC analysis showed 95% product and 5% starting material remaining. The mixture was cooled to 25 C and 290 mL water was added dropwise over a period of 30-40 min. Stirring was continued over night at 23 C. The dark purple solid was collected by filtration, washed with 2× withMeCN/water 1/1 dried at 50 C in vacuo for 15 h to give 218.5 g (88%) product.

Provenance & Evidence