Thiazole → 3-[7-(trans-3-Hexadecyloxytetrahydropyran-2-ylmethoxy)heptyl]thiazolium methanesulfonate

HRID 329497Notes

Reaction equation

HRID 329497 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][C@H:15]1[C@H:20]([O: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][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:19][CH2:18][CH2:17][O:16]1)(=[O:4])=[O:3].[S:38]1[CH:42]=[CH:41][N:40]=[CH:39]1>C1(C)C=CC=CC=1>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH2:22]([O:21][C@@H:20]1[CH2:19][CH2:18][CH2:17][O:16][C@H:15]1[CH2:14][O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][N+:40]1[CH:41]=[CH:42][S:38][CH:39]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 9256ThiazoleHCID 186371317-(trans-3-Hexadecyloxytetrahydropyran-2-ylmethoxy)heptyl methanesulfonate

Product 1

HCID 186371263-[7-(trans-3-Hexadecyloxytetrahydropyran-2-ylmethoxy)heptyl]thiazolium methanesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.20 g of the methanesulfonate [prepared as described in step (a) above] and 1.56 ml of thiazole were dissolved in 3 ml of toluene, and the solution was stirrd on an oil bath kept at 70° C. for 5 days. At the end of this time, the mixture was allowed to cool, the solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography through 40 g of silica gel. 0.741 g of the title compound was obtained as a viscous oil from the fractions eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water.

Workup

  1. customthe solution was stirrd on an oil bath
  2. temperatureto cool
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-30aca703d20b46deb31f4950a25bb076
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

Loading…