Thionyl Chloride → HCID 59804979, compound

HRID 494363Notes

Reaction equation

HRID 494363 reaction equation
S(Cl)([Cl:3])=O.[Na+].[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O-:33])(=O)=[O:31])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:6][C:7]1[O:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([Cl:3])(=[O:33])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59804977HCID 59804977, compound

Product 1

HCID 59804979HCID 59804979, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of thionyl chloride (3.0 mL) and 2 drops of DMF stirring under nitrogen at 0° C. is added the title B compound, 4-(5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy)-benzenesulfonic acid sodium salt (1.1 g, 2.53 mmol) in one portion. The resulting suspension is stirred at 0° C. for 10 min. The ice bath is removed and the suspension is stirred at RT for 3 h. The solution is concentrated and the resulting residue is azeotrophed twice with toluene. The residue is taken up into DCM, filtered and evaporated at reduced pressure to give 4-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonic acid chloride as an oil. It is used as such without any additional purification.

Workup

  1. customThe ice bath is removed
  2. stirringthe suspension is stirred at RT for 3 h
  3. concentrationThe solution is concentrated
  4. filtrationfiltered
  5. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-a33bbcbb5852400f8fdee12e5a0a4202
Source dataset
uspto-grants-2009_05
Patent number
US07538135B2

Reaction notes

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