5-Methylthiazole → 5-Methyl-3-[[3-[[4-(tetradecyloxy)benzoyl]amino]phenyl]methyl]thiazolium bromide

HRID 483562Notes

Reaction equation

HRID 483562 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:32])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:33][C:34]1[S:38][CH:37]=[N:36][CH:35]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:33][C:34]1[S:38][CH:37]=[N+:36]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10](=[O:32])[C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=3)[CH:4]=2)[CH:35]=1

Participants

4

Reactant 2

HCID 1379805-MethylthiazoleHCID 11755784N-[3-(Bromomethyl)phenyl]-4-(tetradecyloxy)benzamide

Product 1

HCID 101001345-Methyl-3-[[3-[[4-(tetradecyloxy)benzoyl]amino]phenyl]methyl]thiazolium bromideYield 91.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4 g of N-[3-(bromomethyl) phenyl]-4-(tetradecyloxy)benzamide and 3.95 g of 5-methylthiazole in 50 ml of toluene is refluxed under argon for 4 hours. The solvent is removed and ether added to the residue. The solid is collected by centrifugation and washed several times with ether then vacuum dried to give 4.4 g of the desired product as a white powder, m.p. 188°-192° C.

Workup

  1. temperatureis refluxed under argon for 4 hours
  2. customThe solvent is removed
  3. additionether added to the residue
  4. customThe solid is collected by centrifugation
  5. washwashed several times with ether
  6. customvacuum dried

Sources & evidence

ORD record
ord-e6b7b0303b6a4438af337e2f4c620249
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Reaction notes

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