Hydrochloric Acid → 184782-88-5

HRID 2301657Notes

Reaction equation

HRID 2301657 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 the thus-obtained 2-(2,4-dihydroxyphenyl)-4,6-diphenyl-s-triazine (17.0 g, 0.05 mol) were added 2-bromoethanol (94.8 g, 0.75 mol) and dimethylformamide, and then a 48% NaOH aqueous solution (29.2 g, NaOH: 0.35 mol) was added dropwise to the mixture at 85° C. The resultant mixture was allowed to react for 10 hours at 85° C. and then cooled, followed by neutralization with concentrated hydrochloric acid. The resultant precipitate was collected through filtration, followed by washing with water and drying, yielding 2-hydroxy-4-(2-hydroxyethyloxy)phenyl-4,6-diphenyl-s-triazine (hereinafter referred to as “HETr”) (15.4 g, 80% yield). To the thus-obtained HETr (15 g, 0.039 mol) were added methacrylic acid (10 g, 0.116 mol), xylene, and p-toluenesulfonic acid (0.6 g), and then the mixture was refluxed at 140° C. for 10 hours. The resultant mixture was washed with water, followed by recrystallization from a solvent mixture of xylene/methanol (1/1), yielding a white solid product having a melting point of 195° C. (15.0 g, 85% yield).

Workup

  1. customto react for 10 hours at 85° C.
  2. temperaturecooled
  3. filtrationThe resultant precipitate was collected through filtration
  4. washby washing with water
  5. customdrying

Sources & evidence

ORD record
ord-baddd6dc053a4080a0238f31fd807ccb
Source dataset
uspto-grants-2002_12
Patent number
US06500887B1

Reaction notes

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