Dimethylamine → Drometrizole

HRID 1030315Notes

Reaction equation

HRID 1030315 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N+:13]([O-])=[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10]1.C1(C)C=CC=CC=1.CNC.[H][H]>[Ni].O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10]1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 1140TolueneHCID 132146462-(2-hydroxy-5-methylphenyl)benztriazole N-oxideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 17113DrometrizoleYield 67%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

24.1 g (0.1 mol) of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole-N-oxide, 9.6g of Raney nickel (produced by Kawaken Fine Chemical Co., Ltd.), 150 ml of a solvent mixture comprising toluene and water (ratio by volume, 4:1) 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 After the air in the flask had been replaced by nitrogen, the resultant mixture was agitated at room temperature.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 bee 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 67% of 2-(2'-hydroxy-5'-methylphenyl)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 12.4 g of 2-(2'-hydroxy-5'-methylphenyl)benzotriazole (yield, 55%; melting point, 128° to 130° 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-22fa5b657e044d4a952816d930f32ddf
Source dataset
uspto-grants-1992_04
Patent number
US05104992

Reaction notes

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