Thionyl Chloride → 4-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride

HRID 643984Notes

Reaction equation

HRID 643984 reaction equation
[Na+].[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O-:25])(=O)=[O:23])=[CH:18][CH:17]=1.S(Cl)([Cl:28])=O>>[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([Cl:28])(=[O:25])=[O:23])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 874004604-(5-Methyl-2-phenyloxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt

Product 1

HCID 210906794-(5-Methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride

Procedure

Thionyl chloride (50 mL) is added to the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt (18.1 g, 52.46 mmol) at 0° C. After 10 min, the ice bath is removed and the mixture is stirred at RT for 30 min. An additional 50 mL of thionyl chloride is added, followed by about 1 mL of DMF. The solid dissolves within 10 min. Stirring is continued for an additional 2.5 h and the mixture is then concentrated under vacuum. The resulting yellow solid is partitioned between 250 mL of water and 250 mL of EtOAc (warm). The organic layer is further washed with water (3×250 mL), 0.1 N aqueous NaOH (4×250 mL) and brine (1×250 mL). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride as a yellow solid: ESI-MS 363.99 [M+1]+.

Workup

  1. customthe ice bath is removed
  2. additionAn additional 50 mL of thionyl chloride is added
  3. dissolutionThe solid dissolves within 10 min
  4. stirringStirring
  5. waitis continued for an additional 2.5 h
  6. concentrationthe mixture is then concentrated under vacuum
  7. customThe resulting yellow solid is partitioned between 250 mL of water and 250 mL of EtOAc (warm)
  8. washThe organic layer is further washed with water (3×250 mL), 0.1 N aqueous NaOH (4×250 mL) and brine (1×250 mL)
  9. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e1b289c85b644dc4b33decebe016ced4
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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