Thionyl Chloride → 4-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazole

HRID 233276Notes

Reaction equation

HRID 233276 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]O)=[CH:18][CH:17]=1.S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][Cl:26])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 118338284-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol

Product 1

HCID 118095944-[2-(4-Chloromethylphenoxy)ethyl]-5-methyl-2-phenyloxazoleYield 90.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol (6.8 g) in chloroform (100 ml) was added thionyl chloride (3.1 g), and the mixture was stirred for one hour at room temperature. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and then water, followed by drying (MgSO4). The solvent was distilled off to leave 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl chloride (6.5 g, 90%) as colorless needles, m.p.93°-94° C.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materialby drying (MgSO4)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-01f8fcbfc83d407e8a9dcfa60ac58dcc
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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