1-Hydroxybenzotriazole → 1-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxide

HRID 1872379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1872379
[OH:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[CH2:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:32]=[CH:31][C:25]([CH:26]=[CH:27][C:28](O)=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH2:14][CH3:15].Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH2:11]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:32]=[CH:31][C:25]([CH:26]=[CH:27][C:28]([N:4]3[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[N+:2]([O-:1])=[N:3]3)=[O:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 540947814-(4-Pentylphenyl)cinnamic acid

Produkt 1

HCID 542184911-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxideAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 1-hydroxybenzotriazole (0.20 g) and 4-(4-pentylphenyl)cinnamic acid (0.40 g) in dichloromethane (12.0 ml) was added 1-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (0.33 g) (WSCD.HCl), and the mixture was stirred for 12 hours at ambient temperature. The reaction mixture was diluted with dichloromethane, and washed with brine, and dried over magnesium sulfate. After magnesium sulfate was filtered off, evaporation of the filtrate and trituration with acetonitrile gave 1-[4-(4-Pentylphenyl)cinnamoyl]benzotriazole 3-oxide (0.24 g).

Aufarbeitung

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter magnesium sulfate was filtered off
  4. customevaporation of the filtrate and trituration with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-27edac2c7ae44f91b9ee746687a03d37
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06107458

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