Dimethylamine → UV-328

HRID 1030312Notes

Reaction equation

HRID 1030312 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N+:22]([O-])=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1.CNC.[H][H]>C1(C)C=CC=CC=1.[C].[Pd]>[OH:1][C:2]1[C:7]([C:8]([CH2:11][CH3:12])([CH3:10])[CH3:9])=[CH:6][C:5]([C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=[CH:4][C:3]=1[N:18]1[N:22]=[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]2=[N:19]1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 111431102-(2H-Benzotriazol-2-yl)-4,6-bis(tert-pentyl)phenol N-oxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 33263UV-328Yield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 1140TolueneSolvent

Procedure

36.7 g (0.1 mol) of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole-N-oxide, 0.125 g of 5% palladium carbon, 150 ml of a toluene solvent and 7 g of 50% dimethylamine were charged into a 500-ml four neck flask. After the air in the flask had been replaced by nitrogen, the resultant mixture was agitated at room temperature. Hydrogen was then supplemented to allow for the amount of hydrogen absorbed by the mixture, which was then subjected to reaction until no more hydrogen was absorbed by it. After the reaction had been completed, the catalyst was filtered off, and part of the filtrate was subjected to quantitative analysis using gas chromatography (GC). The results revealed a yield of 93% of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole. The solvent was then distilled off from the filtrate, and the residual solid was crystallized using ethanol and then washed with ethanol to obtain 28.1 g of 2-(2'-hydroxy-3',5'-di-t-amylphenyl)benzotriazole (yield, 80%; melting point, 79° to 81° C.).

Workup

  1. customabsorbed by the mixture, which
  2. customwas then subjected to reaction until no more hydrogen
  3. customwas absorbed by it
  4. filtrationthe catalyst was filtered off

Sources & evidence

ORD record
ord-26b60e79536d4bc29ce2ec895247c0e0
Source dataset
uspto-grants-1992_04
Patent number
US05104992

Reaction notes

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