Dibutyltin oxide → 2,2'-{(Dibutylstannylene)bis[oxy-(5-tert-octyl-2,l-phenylene)]}bis-(2H-benzotriazole)

HRID 411939

Reaction equation

HRID 411939 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[N:17]1.[CH2:25]([Sn:29](=[O:34])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>C1(C)C=CC=CC=1>[CH2:25]([Sn:29]([CH2:30][CH2:31][CH2:32][CH3:33])([O:34][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:9])[CH3:10])=[CH:4][C:3]=1[N:16]1[N:17]=[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]2=[N:20]1)[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:9])[CH3:10])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[N:17]1)[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 61221Dibutyltin oxideHCID 62485Octrizole

Product 1

HCID 700158602,2'-{(Dibutylstannylene)bis[oxy-(5-tert-octyl-2,l-phenylene)]}bis-(2H-benzotriazole)Yield 43.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

2-(2-Hydroxy-5-tert-octylphenyl)-2H-benzotriazole (64.6 g, 0.2 mol, TINUVIN® 329, CIBA), dibutyltin oxide (24.89 g, 0.1 mol) and toluene are charged to a laboratory reactor and the contents are heated to reflux and refluxed for seven hours. About half of the amount of toluene is removed by distillation. The reaction mass is cooled to 0-5° C. after the addition of 200 g of hexane. Any unreacted TINUVIN® 329 and dibutyltin oxide are removed by filtration. The solvent is then removed by distillation to yield the title compound (38 g, 43.3% yield) as a yellow resin whose structure is consistent with 1Hnmr analysis.

Workup

  1. temperaturethe contents are heated
  2. temperatureto reflux
  3. temperaturerefluxed for seven hours
  4. customAbout half of the amount of toluene is removed by distillation
  5. additionafter the addition of 200 g of hexane
  6. customAny unreacted TINUVIN® 329 and dibutyltin oxide are removed by filtration
  7. customThe solvent is then removed by distillation

Sources & evidence

ORD record
ord-3960e0e1cbd14cc2a22ad5d9b26cedfc
Source dataset
uspto-grants-2003_05
Patent number
US06562085B1

Linked notes

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