Thionyl Chloride → 4-(Chloromethyl)-5-methyl-2-(4-methylphenyl)-1,3-oxazole

HRID 22250Notes

Reaction equation

HRID 22250 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19430222HCID 19430222, compound

Product 1

HCID 50764854-(Chloromethyl)-5-methyl-2-(4-methylphenyl)-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-hydroxymethyl-2-(4-methylphenyl)-5-methyl-1,3-oxazole (3 g) in 30 ml of dichloromethane was cooled to 0° C., and thionyl chloride (1.75 g) added dropwise. The reaction was stirred for 1 hour at room temperature, then washed twice with dilute sodium bicarbonate solution, the organic layer separated, dried over sodium sulfate, and the solvent evaporated under reduced pressure, to yield 4-chloromethyl-2-(4-methylphenyl)-5-methyl-l,3-oxazole, which was used in the next reaction without further purification.

Workup

  1. washwashed twice with dilute sodium bicarbonate solution
  2. customthe organic layer separated
  3. dry with materialdried over sodium sulfate
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-907e8a3271eb451eb04e801c9d881b52
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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