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) δ 2.1 (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-f5a7a9e92475489387f0108b567a2075

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06942966B1