HCID 22035097, compound → HCID 21708822, compound

HRID 2287642Notes

Reaction equation

HRID 2287642 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2=[N:6][N:7]([C:9]3[CH:14]=[C:13]([CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])[CH:12]=[CH:11][C:10]=3[OH:23])[N:8]=[C:4]2[CH:3]=1.[CH3:26][O-:27].[Na+].CO>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:3]2[C:4](=[N:8][N:7]([C:9]3[C:10]([OH:23])=[C:11]([CH2:10][C:11]4[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([N:7]5[N:6]=[C:5]6[CH:24]=[CH:25][CH:2]=[CH:3][C:4]6=[N:8]5)[C:26]=4[OH:27])[CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:18](=[O:22])[C:19]([CH3:21])=[CH2:20])[CH:14]=3)[N:6]=2)[CH:5]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 22035097HCID 22035097, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 21708822HCID 21708822, compoundYield 70.3%

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 11.1 g (31.0 mmols) of 5-chloro-2-(2'-hydroxy-5'-methacryloyloxyethylphenyl)-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 13.1 g of 6-(4-chloro-2H-benzotriazol-2-yl)-4-methacryloyloxyethyl-2-[3'-(2H-benzotriazol-2-yl)-2'-hydroxy-5'-methylphenyl]methylphenol (hereinafter abbreviated as "RUVA-2") as white crystals (yield 70.3%, purity 98.8%).

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-eddfc1a75f61478dbb491430bcdb56f0
Source dataset
uspto-grants-2000_07
Patent number
US06084104

Reaction notes

Loading…