Pyridine → 2-Phenyl-4-(2-hydroxy-4-hexyloxyphenyl)-6-[2-hydroxy-4-(11-methacryloyloxy-undecyloxy)-phenyl]-1,3,5-triazine

HRID 1735913Notes

Reaction equation

HRID 1735913 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[OH:26])[N:10]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][OH:45])=[CH:29][C:28]=3[OH:46])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:47](Cl)(=[O:51])[C:48]([CH3:50])=[CH2:49].N1C=CC=CC=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:15][C:14]=3[OH:26])[N:10]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:45][C:47](=[O:51])[C:48]([CH3:50])=[CH2:49])=[CH:29][C:28]=3[OH:46])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 1362052792-Phenyl-4-(2-hydroxy-4-n-hexyloxy-phenyl)-6-[2-hydroxy-4-(11-hydroxy-undecyloxy)-phenyl]-1,3,5-triazine

Product 1

HCID 1360232012-Phenyl-4-(2-hydroxy-4-hexyloxyphenyl)-6-[2-hydroxy-4-(11-methacryloyloxy-undecyloxy)-phenyl]-1,3,5-triazineYield 91.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
55 °C

Procedure

The reaction is carried out under nitrogen protection. A mixture of 22.0 g (35.0 mmoles) of 2-phenyl-4-(2-hydroxy-4-n-hexyloxy-phenyl)-6-[2-hydroxy-4-(11-hydroxy-undecyloxy)phenyl]-1,3,5-triazine, 4.4 g (42.0 mmoles) of methacryloyl chloride (Fluka, 97% ), 0.5 g (6.3 mmoles) of pyridine in 100 mL of toluene (Merck, 99.5%) are heated at 80°-85° C. for 21 hours. After cooling to 55° C., there are added 8.9 g (87.5 mmoles) of triethylamine (Fluka, 99.5%). The mixture is heated at 80° C. for further 7 hours then filtered hot. The filtrate is evaporated. The crude product (25.7 g ) is dissolved in 120 mL of CH2Cl2, filtered through a Kieselgel 60 pad (230-400 mesh; 6.5 cm diameter; h=5 cm) and eluted with 380 mL of CH2Cl2. Solvent removal and drying at 80° C./0.1 mmHg for 2 hours 30 min. give 22.3 g (91.4% yield ) of 2-phenyl-4-(2-hydroxy-4-hexyloxyphenyl)-6-[2hydroxy-4-(11-methacryloyloxy-undecyloxy)-phenyl]-1,3,5-triazine, as an orange resin, Tg=-13° C. (DSC).

Workup

  1. temperatureare heated at 80°-85° C. for 21 hours
  2. temperatureThe mixture is heated at 80° C. for further 7 hours
  3. filtrationthen filtered hot
  4. customThe filtrate is evaporated
  5. dissolutionThe crude product (25.7 g ) is dissolved in 120 mL of CH2Cl2
  6. filtrationfiltered through a Kieselgel 60 pad (230-400 mesh; 6.5 cm diameter; h=5 cm)
  7. washeluted with 380 mL of CH2Cl2
  8. customSolvent removal
  9. customdrying at 80° C./0.1 mmHg for 2 hours 30 min.

Sources & evidence

ORD record
ord-e26aeef05d004ccaacb394df329027d6
Source dataset
uspto-grants-1996_07
Patent number
US05538840

Reaction notes

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