Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21840895, compound

HRID 1739378Notes

Reaction equation

HRID 1739378 reaction equation
C(OC([O:6][CH2:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH:10]([C:13]1[S:17][CH2:16][N:15]([CH3:18])[CH:14]=1)[O:11][CH3:12])C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Cl-].[Na+].O>[OH:6][CH2:7][C:8]1[CH:22]=[CH:21][CH:20]=[CH:19][C:9]=1[CH:10]([C:13]1[S:17][CH2:16][N:15]([CH3:18])[CH:14]=1)[O:11][CH3:12]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21840899HCID 21840899, compound

Product 1

HCID 21840895HCID 21840895, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To 3.05 g (10 mmol) of 5-[2-(1-ethoxyethyl)oxymethyl-α-methoxybenzyl]-3-methylthiazole was added 0.25 g (1 mmol) of pyridinium p-toluenesulfonate and stirred under reflux for an hour. After completion of the reaction, 150 ml of brine was added and extracted twice with 80 ml of dichloromethane. The extract was dried over anhydrous magnesium and concentrated under reduced pressure to give 5-(2-hydroxymethyl-α-methoxybenzyl)-3-methylthiazole (2.33 g, 99.9%) as colorless oil.

Workup

  1. temperatureunder reflux for an hour
  2. additionwas added
  3. extractionextracted twice with 80 ml of dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d771fe3ccaa747f68fdce23c29f98568
Source dataset
uspto-grants-1999_10
Patent number
US05965740

Reaction notes

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