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

HRID 484600Notes

Reaction equation

HRID 484600 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O: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][CH2:32][CH3:33])=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:34][C:35]1[S:39][CH:38]=[N:37][CH:36]=1>O1CCCC1>[Br-:1].[CH3:34][C:35]1[S:39][CH:38]=[N+:37]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([O: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][CH2:32][CH3:33])=[CH:15][CH:14]=3)=[O:11])[CH:4]=2)[CH:36]=1

Participants

4

Reactant 2

HCID 1379805-MethylthiazoleHCID 10481690N-[3-(Bromomethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea

Product 1

HCID 104614835-Methyl-3-[[3-[[[[4-(tetradecyloxy)phenyl]amino]carbonyl]amino]phenyl]methyl]thiazolium bromideYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4 g of N-[3-(bromomethyl)phenyl]-N'-[4-(tetradecyloxy)phenyl]urea and 2.3 g of 5-methylthiazole in 60 ml of tetrahydrofuran is refluxed for 4 hours. The solvent is evaporated, toluene added to the residue and evaporated to a residue. The residue is stirred with ether and the solid collected, washed with fresh ether and dried under vacuum to give 4.7 g of the desired product as a white powder, m.p. 165°-168° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. customThe solvent is evaporated
  3. additiontoluene added to the residue
  4. customevaporated to a residue
  5. customthe solid collected
  6. washwashed with fresh ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-aedb70e365a54577961c816279b4f3c2
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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