Dimethylamine → 2,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenol

HRID 1030317Notes

Reaction equation

HRID 1030317 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[N:16]1[N+:20]([O-])=[C:19]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:18]2=[N:17]1.C1(C)C=CC=CC=1.CNC.[H][H]>[C].[Pd].O.CC(O)CC>[OH:1][C:2]1[C:7]([C:8]([CH3:10])([CH3:11])[CH3:9])=[CH:6][C:5]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:4][C:3]=1[N:16]1[N:20]=[C:19]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:18]2=[N:17]1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 1140TolueneHCID 141494712-(2-hydroxy-3,5-di-t-butylphenyl)-5-chlorobenzotriazole-N-oxideHCID 178418361HCID 178418361, compound3×

Product 1

HCID 774702,4-Di-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)phenolYield 84.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 6568(+-)-2-ButanolSolvent

Procedure

37.4 g (0.1 mol) of 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole-N-oxide, 0.125 g of palladium carbon, 300 ml of a solvent mixture comprising toluene, 2-butanol and water (ratio by volume of 10:7:10) and 5 g of 50% dimethylamine were charged into a 500- ml stainless autoclave equipped with an agitator. After the air in the autoclave had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2. The temperature of the resultant mixture was increased to 60° C. under agitation, and reaction was been effected while agitation being continued until no more hydrogen was absorbed by the mixture. After the reaction had been completed, the autoclave was cooled, and the catalyst was filtered off. After most part of the solvent had been distilled off from the filtrate, the residual solid was washed with ethanol and dried to obtain 30.4 g of 2-(2'-hydroxy-3',5'-di-t-butylphenyl)-5-chlorobenzotriazole as a target substance (yield, 85.0%; melting point, 153° to 155° C.).

Workup

  1. additionwere charged into a 500- ml stainless autoclave
  2. customequipped with an agitator
  3. customwas absorbed by the mixture
  4. temperaturethe autoclave was cooled
  5. filtrationthe catalyst was filtered off
  6. distillationAfter most part of the solvent had been distilled off from the filtrate
  7. washthe residual solid was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-eb817557ccfc4dc68ec0f097021d1cde
Source dataset
uspto-grants-1992_04
Patent number
US05104992

Reaction notes

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