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

HRID 653764Notes

Reaction equation

HRID 653764 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.C[C:35]1[S:39][CH:38]=[N:37][CH:36]=1.[CH3:40]COCC>C1(C)C=CC=CC=1>[Br-:1].[CH3:40][N+:37]1([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]=[CH:35][S:39][CH2:38]1

Participants

5

Reactant 3

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

Product 1

HCID 198895573-Methyl-3-[[2-[[[4-(tetradecyloxy)phenyl]acetyl]amino]phenyl]methyl]thiazolium bromide

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-572c7bc9eaba4f78a82cb2d187365c8a
Source dataset
uspto-grants-1992_07
Patent number
US05128351

Reaction notes

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