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

HRID 351021Notes

Reaction equation

HRID 351021 reaction equation
S(Cl)([Cl:3])=O.[Na+].[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O-:29])(=O)=[O:27])=[CH:22][CH:21]=1>CN(C)C=O>[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:3])(=[O:29])=[O:27])=[CH:22][CH:21]=1

Participants

4

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of thionyl chloride (8.0 mL) and 2 drops of N,N-dimethylformamide stirring under nitrogen at 0° C. is added the title B compound, 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt (1.42 g, 3.8 mmol) in one portion. The resulting suspension is stirred at 0° C. for 10 minutes. The ice bath is removed and the suspension is stirred at room temperature for 1.5 hours. Three more drops of N,N-dimethyl-formamide is added, after which a clear solution results upon stirring for an additional hour. The solution is concentrated under vacuo to a solid residue. The residue is partitioned between water (20 mL) and ethyl acetate (20 mL). The organic layer is separated and washed successively with water (3×20 mL), 0.1N aqueous sodium hydroxide (3×20 mL) and brine (20 mL). The organic layer is dried over anhydrous MgSO4, filtered and concentrated in vacuo to give an oil which slowly solidifies to give 0.48 g of 4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzenesulfonyl chloride: [M+1]+=363.99.

Workup

  1. customThe ice bath is removed
  2. stirringthe suspension is stirred at room temperature for 1.5 hours
  3. additionThree more drops of N,N-dimethyl-formamide is added
  4. customafter which a clear solution results
  5. stirringupon stirring for an additional hour
  6. concentrationThe solution is concentrated under vacuo to a solid residue
  7. customThe residue is partitioned between water (20 mL) and ethyl acetate (20 mL)
  8. customThe organic layer is separated
  9. washwashed successively with water (3×20 mL), 0.1N aqueous sodium hydroxide (3×20 mL) and brine (20 mL)
  10. dry with materialThe organic layer is dried over anhydrous MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customto give an oil which

Sources & evidence

ORD record
ord-c480072b39454333b30a0e26177b26ee
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Reaction notes

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