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

HRID 1647587Notes

Reaction equation

HRID 1647587 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 103718203-[[3-[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]phenyl]methyl]-5-methylthiazolium bromideYield 87.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-6d8e874ce7f1400cae6bd6326ea65c57
Source dataset
uspto-grants-1995_07
Patent number
US05432189

Reaction notes

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