5-Methylthiazole → 3-[[3-[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]phenyl]methyl]-5-methylthiazolium bromide

HRID 484596

Reaktionsgleichung

Reaktionsgleichung von HRID 484596
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[CH3:35][C:36]1[S:40][CH:39]=[N:38][CH:37]=1>C1(C)C=CC=CC=1.CCOCC>[Br-:1].[C:10]([N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=1)[C:5]1[CH:4]=[C:3]([CH2:2][N+:38]2[CH:37]=[C:36]([CH3:35])[S:40][CH:39]=2)[CH:8]=[CH:7][CH:6]=1)(=[O:12])[CH3:11]

Komponenten

5

Edukt 2

HCID 1379805-MethylthiazoleHCID 10414650N-[3-(bromomethyl)phenyl]-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide

Produkt 1

HCID 103718203-[[3-[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]phenyl]methyl]-5-methylthiazolium bromideAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 3 g of N-[3-(bromomethyl)phenyl]-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide and 2.24 g of 5-methylthiazole in 40 ml of toluene is refluxed for 4 hours, cooled and diluted with 60 ml of ether and allowed to stand at room temperature overnight. The solid is collected by centrifugation and washed three times with ether then vacuum dried to give 3.1 g of the desired product as a white powder, m.p. 130°-134° C.

Aufarbeitung

  1. temperatureis refluxed for 4 hours
  2. temperaturecooled
  3. customThe solid is collected by centrifugation
  4. washwashed three times with ether
  5. customvacuum dried

Quellen und Nachweise

ORD-Eintrag
ord-1c13823ac4cf4a98ae483ed0a87c9ec6
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231182

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