Hydrochloric Acid → 184782-88-5

HRID 2270888Notes

Reaction equation

HRID 2270888 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:12]=[C:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1.Br[CH2:28][CH2:29][OH:30].[OH-].[Na+].Cl>CN(C)C=O>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:28][CH2:29][OH:30])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 1354371252-(2,4-Dihydroxyphenyl)-4,6-diphenyl-1,3,5-triazine

Product 1

HCID 135774071184782-88-5Yield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 17.0 g (0.05 mol) of the resulting 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-s-triazine were added 94.8 g (0.75 mol) of 2-bromoethanol and 85 g of dimethylformamide, and 29.2 g (0.35 mol) of a 48% aqueous solution of sodium hydroxide was added thereto dropwise at 85° C. The mixture was allowed to react at 85° C. for 10 hours, followed by cooling. The reaction mixture was neutralized with concentrated hydrochloric acid, and the precipitate was collected by filtration, washed with water, and dried to give 15.4 g (80%) of 2-hydroxy-4-(2-hydroxyethyloxy)phenyl-4,6-diphenyl-s-triazine (hereinafter referred to as HETr). To 15 g (0.039 mol) of the resulting HETr were added 6.8 g (0.047 mol) of octylic acid, 45 g of xylene, and 0.6 g of p-toluenesulfonic acid, and the mixture was heated under reflux at 140° C. for 10 hours. The reaction mixture was washed with water and recrystallized from a 1:3 mixed solvent of xylene and methanol to give 16.9 g (85%) of a pale yellow solid having a melting point of 109° C.

Workup

  1. additionwas added
  2. customdropwise at 85° C
  3. customto react at 85° C. for 10 hours
  4. temperatureby cooling
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-06531165b10a40c9aa79505cae10c6c3
Source dataset
uspto-grants-2001_12
Patent number
US06333114B1

Reaction notes

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