HCID 21987688, compound → HCID 21708852, compound

HRID 651553Notes

Reaction equation

HRID 651553 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])=[CH:4][C:3]=1[N:15]1[N:19]=[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]2=[N:16]1.[CH3:24][O-:25].[Na+].[CH3:27][OH:28]>C1(C)C(C)=CC=CC=1>[N:19]1[N:15]([C:3]2[C:24]([OH:25])=[C:7]([CH2:2][C:7]3[CH:6]=[C:5]([CH3:8])[CH:4]=[C:3]([N:15]4[N:16]=[C:17]5[CH:23]=[CH:22][CH:21]=[CH:20][C:18]5=[N:19]4)[C:27]=3[OH:28])[CH:6]=[C:5]([CH2:8][CH2:9][O:10][C:11](=[O:14])[CH:12]=[CH2:13])[CH:4]=2)[N:16]=[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=12

Participants

4

Reactant 2

HCID 21987688HCID 21987688, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 21708852HCID 21708852, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ten grams (30.9 mmols) of crude 2-(3′-N,N-diethylaminomethyl-2′-hydroxy-5′-methylphenyl)-2H-benzotriazole obtained following the procedures of Synthesis Example 1 and 9.57 g (30.9 mmols) of 2-(2′-hydroxy-5′-acryloyloxyethylphenyl)-2H-benzotriazole were dissolved in 64 ml of xylene, and 1.5 ml of a 28% sodium methylate•methanol solution were added thereto. The mixture was then refluxed in a nitrogen stream for 10 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature. Yellow crystals precipitated at this stage were separated through filtration, and recrystallized from chloroform to obtain 11.8 g of 6-(2H-benzotriazol-2-yl)-4-acryloyloxyethyl-2-[3′-(2H-benzotriazol-2-yl)-2′-hydroxy-5′-methylphenyl]methylphenol (hereinafter abbreviated as “RUVA-4”) as white crystals (yield 69.1%, purity 99.0%).

Workup

  1. temperatureThe mixture was then refluxed in a nitrogen stream for 10 hours
  2. customAfter the completion of the reaction
  3. customYellow crystals precipitated at this stage
  4. customwere separated through filtration
  5. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-f38947ef777b46a98ab4eb25a5f83656
Source dataset
uspto-grants-2001_08
Patent number
US06281313B1

Reaction notes

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