2-(3'-tert-Butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazole → N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamamide

HRID 1493413

Reaktionsgleichung

Reaktionsgleichung von HRID 1493413
[N:1]1[N:2]([C:10]2[CH:11]=[C:12]([CH:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=2[OH:22])[CH2:13][CH2:14][C:15](OC)=[O:16])[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[NH2:27][CH:28]1[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:30]([CH3:46])([CH3:45])[CH2:29]1>C(OCC)(=O)C>[CH2:37]([O:36][N:31]1[C:32]([CH3:35])([CH3:34])[CH2:33][CH:28]([NH:27][C:15](=[O:16])[CH2:14][CH2:13][C:12]2[CH:19]=[C:20]([C:23]([CH3:24])([CH3:25])[CH3:26])[C:21]([OH:22])=[C:10]([N:2]3[N:3]=[C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]4=[N:1]3)[CH:11]=2)[CH2:29][C:30]1([CH3:45])[CH3:46])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

4

Edukt 2

HCID 934812-(3'-tert-Butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)benzotriazoleHCID 233720934-Amino-N-octyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 21645439N-(1-Octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamamideAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4.0 g (11.3 mmol) of methyl 3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate and 8.0 g (28.1 mmol) of 4-amino-1-octyloxy-2,2,6,6-tetramethylpiperidine is heated at 190°-200° C. for 2 hours. The reaction mixture is dissolved in ethyl acetate (300 ml). The organic solution is washed with 1N hydrochloric acid (2 ×100 ml) and saturated sodium bicarbonate solution (200 ml), then dried over magnesium sulfate and evaporated to obtain a solid. Purification by flash chromatography on silica gel (3:1 heptane: ethyl acetate) following by recrystallization from methanol affords 1.0 g (15% yield) of the title compound, a white solid, mp 153°-9° C.

Aufarbeitung

  1. temperatureis heated at 190°-200° C. for 2 hours
  2. washThe organic solution is washed with 1N hydrochloric acid (2 ×100 ml) and saturated sodium bicarbonate solution (200 ml)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto obtain a solid
  6. customPurification by flash chromatography on silica gel (3:1 heptane: ethyl acetate)
  7. customfollowing by recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-62193cd13d364ebcb097d26237458510
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021478

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