Thionyl Chloride → Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylate

HRID 1716825Notes

Reaction equation

HRID 1716825 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 46834789Ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate

Product 1

HCID 46834790Ethyl 2-[4-(chloromethyl)phenyl]-1,3-oxazole-4-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methylene chloride at −10° C. and excess thionyl chloride was added portionwise ethyl 2-[4-(hydroxymethyl)phenyl]-1,3-oxazole-4-carboxylate (1 eq) and the resulting mixture was stirred at room temperature for 3 h. The solvent was removed and the residue was azeotroped with toluene, dissolved in methylene chloride, washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give a yield of 96% of the product as white crystals; m.p. 115-117° C. 1H NMR (300 MHz, CDCl3, δ): 8.28 (s, 1H), 8.12 (d, 2H, J=8.5 Hz), 7.50 (d, 2H, J=8.5 Hz), 4.62 (s, 2H), 4.43 (m, 2H, J=7.4 Hz), 1.41 (t, 3H, J=7.4 Hz).

Workup

  1. customThe solvent was removed
  2. customthe residue was azeotroped with toluene
  3. dissolutiondissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c2042fb571624d4381a6a957afff6cec
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

Loading…