Diethyl Ether → 5-Methyl-3-[[2-[[[4-(tetradecyloxy)phenyl]acetyl]amino]phenyl]methyl]thiazolium bromide

HRID 1647570Notes

Reaction equation

HRID 1647570 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:33])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=1.[CH3:34][C:35]1[S:39][CH:38]=[N:37][CH:36]=1.CCOCC>C1(C)C=CC=CC=1>[Br-:1].[CH3:34][C:35]1[S:39][CH:38]=[N+:37]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[NH:9][C:10](=[O:33])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[CH:14][CH:13]=2)[CH:36]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 1379805-MethylthiazoleHCID 10391829N-[2-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide

Product 1

HCID 104387945-Methyl-3-[[2-[[[4-(tetradecyloxy)phenyl]acetyl]amino]phenyl]methyl]thiazolium bromideYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.0 g of N-[2-(bromomethyl)phenyl]-4-(tetradecyloxy)benzeneacetamide and 2.88 g of 5-methylthiazole in 25 ml of toluene is heated at reflux under argon for 2.5 hours. The mixture is poured into 200 ml of ether, cooled, the solid collected, washed with ether and dried to give 3.2 g of the desired product as a white powder, m.p. 124°-127° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under argon for 2.5 hours
  3. temperaturecooled
  4. customthe solid collected
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-52249ea8fad4489885e10c536cb2a43f
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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