Ethanol → HCID 12606420, compound

Participants

Reaction Conditions

Reaction Steps

Solid NaOH (187.2 g, 4541 mmol) was added to EtOH (2000.0 mL, 34253 mmol) at rt and stirred until disolved. The solution was cooled to 15° C. and malononitrile (150 g, 2300 mmol) was added in one portion and the resulting suspension was stirred until the malononitrile had dissolved (reaction is slightly endothermic). The reaction mixture was stirred for 1 h and carbon disulfide (136.6 mL, 2271 mmol) was added while keeping the temperature between 10 and 20° C. After about half of the carbon disulfide was added the reaction mixture begins to solidify and becomes very difficult to stir. The addition of carbon disulfide was continued and the reaction was stirred mechanically with a spatula. When the addition was complete the reaction mixture was warmed to 30° C. and then cooled to room temperature. The product was filtered and dried under vacuum at 82° C. for 2 days. The solid material obtained was ground up with a mortor and pestal and then dried under vacuum to give the title compound (335 grams, 79%).

Provenance & Evidence