Dimethylamine → Octrizole

HRID 2082167Notes

Reaction equation

HRID 2082167 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[N:11][C:12]1[CH:17]=[C:16]([C:18]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19])[CH:15]=[CH:14][C:13]=1[OH:26])([O-])=O.C1(C)C=CC=CC=1.CNC.[H][H]>[C].[Pd].O.CC(O)C>[OH:26][C:13]1[CH:14]=[CH:15][C:16]([C:18]([CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:19])=[CH:17][C:12]=1[N:11]1[N:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]2=[N:1]1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 1140TolueneHCID 1039272-((2-Nitrophenyl)azo)-4-(1,1,3,3-tetramethylbutyl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 62485OctrizoleYield 82.9%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

35.5 g (0.1 mol) of 2-nitro-2'-hydroxy-5'-t-octylazobenzene, 0.125 g of 5% palladium carbon, 100 ml of toluene, 100 ml of IPA, 50 ml of water and 7 g of 50% dimethylamine were charged into a 500-ml stainless autoclave with an agitator. Reaction was effected in the same way as that employed in Example 1 and stopped when no more hydrogen was absorbed by the reaction solution. After the reaction had been completed, after treatment was performed in the same way as in Example 1 to obtain 26.8 g of 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole (yield, 82.9%; melting point, 103° to 105° C.).

Workup

  1. customReaction
  2. customwas absorbed by the reaction solution

Sources & evidence

ORD record
ord-c1e2e4de03f149e0b8cb463df1f2b79a
Source dataset
uspto-grants-1993_02
Patent number
US05187289

Reaction notes

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