Dimethylformamide → HCID 77230956, compound

Temperature

0 °C

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.

1. customThe resulting reaction mixture
2. temperatureto slowly warm to room temperature
3. customA small amount of solid precipitated out of the solution at which
4. additionwas added
5. filtrationThe product was filtered off through a coarse Buchner funnel with the aid of water
6. dry with materialAfter drying under vacuum, batch #1 of 3-(4-chloro-1,3,5-triazin-2-ylamino)-N-methylbenzamide
7. customwas obtained (7.15 g, 58% yield) as a yellow solid
8. extractionThe filtrate was extracted with CH2Cl2 (3×100 mL)
9. customThe organic layer was separated
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-9a2bed7f5edf47898be38332b4591b93

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334269B2