Dimethylformamide → HCID 77230956, compound

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-1,3,5-triazine (6.99 g, 46.6 mmol) was dissolved in DMF (56.5 mL, 46.6 mmol) and the solution was cooled to 0° C. To this solution was added N-ethyl-N-isopropylpropan-2-amine (8.93 mL, 51.3 mmol) followed by the portionwise addition of 3-amino-N-methylbenzamide (7.00 g, 46.6 mmol). The resulting reaction mixture was allowed to slowly warm to room temperature and stirred for 4 hours. Water (about 800 mL) was added to the reaction mixture. A small amount of solid precipitated out of the solution at which point 100 mL of CH2Cl2 was added. The product was filtered off through a coarse Buchner funnel with the aid of water. After drying under vacuum, batch #1 of 3-(4-chloro-1,3,5-triazin-2-ylamino)-N-methylbenzamide was obtained (7.15 g, 58% yield) as a yellow solid. The filtrate was extracted with CH2Cl2 (3×100 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated, providing an additional batch of material (2.4 g, 20%) as yellow solid.

Provenance & Evidence