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 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, 85.7mmole) 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-b767851333de4e96b0c6846c58512ecf

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06207826B1