Thionyl Chloride → HCID 67547597, compound

HRID 2356730Notes

Reaction equation

HRID 2356730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH2:20]O)=[CH:4][C:3]=1[F:22].S(Cl)([Cl:25])=O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:10][C:9]=2[CH2:20][Cl:25])=[CH:4][C:3]=1[F:22]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 67547273HCID 67547273, compound

Product 1

HCID 67547597HCID 67547597, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-chloro-3-fluorophenyl)-2-(4-fluoro-phenyl)-4-hydroxymethyloxazole (965 mg) and thionyl chloride (1.1 ml) in tetrahydrofuran (30 ml) was stirred at 0° C. for 30 minutes, followed by stirring at room temperature for 2 hours. Additional thionyl chloride (1.1 ml) was added to the mixture and the mixture was refluxed for one hour. The reaction mixture was concentrated under reduced pressure. The remaining volatiles were removed by evaporation with toluene, and further dried under reduced pressure to obtain a crude product of 5-(4-chloro-3-fluorophenyl)-4-chloromethyl-2-(4-fluoro-phenyl)oxazole (925 mg).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe remaining volatiles were removed by evaporation with toluene
  4. customfurther dried under reduced pressure

Sources & evidence

ORD record
ord-69edea7ed4a64982994c8944cceaf9dc
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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