Dimethylamine → Tinuvin

HRID 1030319

Reaktionsgleichung

Reaktionsgleichung von HRID 1030319
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[N:13]1[N+:17]([O-])=[C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]2=[N:14]1.C1(C)C=CC=CC=1.CNC.[H][H]>[C].[Pd].O.C(O)CCC>[OH:1][C:2]1[C:7]([C:8]([CH3:10])([CH3:9])[CH3:11])=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[N:13]1[N:17]=[C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]2=[N:14]1

Komponenten

8

Edukt 4

HCID 674DimethylamineHCID 1140TolueneHCID 141494702-(2-hydroxy-3-t-butyl-5-methylphenyl)-5-chlorobenzotriazole-N-oxideHCID 178418361HCID 178418361, Verbindung3×

Produkt 1

HCID 62531TinuvinAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 2631-ButanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

33.2 g (0.1 mol) of 2-(2'-hydroxy-3'-t-butyl-5'-methylphenyl)-5-chlorobenzotriazole-N-oxide, 0.125 g of palladium carbon, 300 ml of a solvent mixture comprising toluene, butanol and water (ratio by volume of 1:1:1) and 5 g 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 After the air in the autoclave had been replaced by hydrogen, the pressure of hydrogen was set to 10 kg/cm2.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 50° C. under agitation, and agitation was continued until no more hydrogen gas was absorbed by the mixture. The pressure of hydrogen was always kept at 8 to 10 kg/cm2 during the reaction. After the reaction had been completed, the autoclave was cooled, and the catalyst was filtered off. The most part of solvent was distilled off, and the residual solid was washed with isopropyl alcohol and then dried to obtain 27.2 g of 2-(2'-hydroxy-3'-t-butyl- 5'-methylphenyl)-5-chlorobenzotriazole as a target substance (yield, 86.2%; melting point, 138° to 140° C.).

Aufarbeitung

  1. additionwere charged into a 500-ml stainless autoclave
  2. customequipped with an agitator
  3. customwas absorbed by the mixture
  4. customThe pressure of hydrogen was always kept at 8 to 10 kg/cm2 during the reaction
  5. temperaturethe autoclave was cooled
  6. filtrationthe catalyst was filtered off
  7. distillationThe most part of solvent was distilled off
  8. washthe residual solid was washed with isopropyl alcohol
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-24723d7b1a7641828cb4c0fff5e4aed4
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05104992

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