Triallyl cyanurate → 2-(3-Azidopropoxy)-4,6-diallyloxy-s-triazine

Temperature

-78 °C

To 3-azido-1-propanol (8.7 g, 85.7 mmol) in THF (200 mL) was added sodium hydride (5.6 g, 128.6 mmol) at −78° C. The reaction mixture was stirred at −78° C. for about 30 minutes and then allowed to equilibrate at room temperature and stirred for an additional 3 hours. The reaction mixture was recooled to −78° C. and added to a solution of 2,4,6-triallyloxy-1,3,5-triazine (21.4 g, 85.7 mmole) in THF (200 mL). The reaction mixture was stirred at room temperature for about 16 hours. The reaction mixture was evaporated to a brown residue. The residue was purified by flash column chromatography over silica gel using EtOAc/hexane as the eluent. The pure fractions were pooled together and evaporated to dryness to give 8.5 g (36%) of the title compound. TLC (Rf: 0.5; 20% EtOAc/Hexane, I2). 1H NMR (CDCl3) δ2.1 (m, 2H, CH2), 3.5 (t, 2H, CH2), 4.5 (t, 2H, CH2), 4.9 (m, 4H, CH2), 4.3 (m. 4H, CH2), 6.0 (m, 2H, CH).

1. customto equilibrate at room temperature
2. stirringstirred for an additional 3 hours
3. customwas recooled to −78° C.
4. stirringThe reaction mixture was stirred at room temperature for about 16 hours
5. customThe reaction mixture was evaporated to a brown residue
6. customThe residue was purified by flash column chromatography over silica gel
7. customevaporated to dryness

ORD record

ord-13645f5423584a64a3c054a68779875c

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559303B1