Dimethylformamide → 2-[2-Hydroxy-5-(1-methyl-1-phenylethyl)-4-octyloxyphenyl]4,6-bis-phenyl-s-triazine

HRID 1077615Notes

Reaction equation

HRID 1077615 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([C:9]([CH3:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])=[CH:4][C:3]=1[C:18]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:21]=[C:20]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:19]=1.CN(C)C=O.[H-].[Na+].Br[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51]>O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[C:5]([C:9]([CH3:17])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])=[CH:4][C:3]=1[C:18]1[N:19]=[C:20]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:21]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 1358436022-[2,4-Dihydroxy-5-(1-methyl-1-phenylethyl)phenyl]-4,6-bis-phenyl-s-triazin

Product 1

HCID 1358435852-[2-Hydroxy-5-(1-methyl-1-phenylethyl)-4-octyloxyphenyl]4,6-bis-phenyl-s-triazineYield 22.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL three-necked, round-bottomed flask equipped with a condenser, magnetic stirrer, thermometer, and a nitrogen atmosphere are charged 4.00 g (8.71 mmol) of the product of Example 9, 50 mL of N,N-dimethylformamide and 0.40 g (10 mmol) of sodium hydride (60 % in mineral oil). The mixture is heated to an external temperature of 50° C. and 1.68 g (8.70 mmol) of 1-bromooctane are added. The mixture is stirred at this temperature for six hours and is allowed to cool to room temperature. The mixture is poured into a beaker of water which is extracted four times with chloroform. The combined chloroform layers are washed four times with water and dried over anhydrous magnesium sulfate and filtered. The solvent is removed under reduced pressure to afford a yellow oil. The crude product is purified with medium pressure chromatography with 10:1 heptane:ethyl acetate followed by recrystallization from acetone/water to yield 1.12 g of the title compound as a yellow solid.

Workup

  1. customTo a 500 mL three-necked, round-bottomed flask equipped with a condenser, magnetic stirrer
  2. additionare added
  3. extractionis extracted four times with chloroform
  4. washThe combined chloroform layers are washed four times with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customto afford a yellow oil
  9. customThe crude product is purified with medium pressure chromatography with 10:1 heptane
  10. customethyl acetate followed by recrystallization from acetone/water

Sources & evidence

ORD record
ord-84e9086e806b4580a1187ff8bddae255
Source dataset
uspto-grants-1996_08
Patent number
US05543518

Reaction notes

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