Thionyl Chloride → 4-(Chloromethyl)-2-phenyl-5-(trifluoromethyl)-1,3-oxazole

HRID 508155Notes

Reaction equation

HRID 508155 reaction equation
[C:1]1([C:7]2[O:8][C:9]([C:14]([F:17])([F:16])[F:15])=[C:10]([CH2:12]O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH2:12][C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:8][C:9]=1[C:14]([F:17])([F:16])[F:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 58118959HCID 58118959, compound

Product 1

HCID 582842954-(Chloromethyl)-2-phenyl-5-(trifluoromethyl)-1,3-oxazole

Procedure

359 mg (1.137 mmol, 76% purity) of the compound from Example 23A are initially charged in 0.63 ml (8.64 mmol) of thionyl chloride. The reaction mixture is stirred at RT for 48 h. After concentration on a rotary evaporator, the residue is taken up in 10 ml of ethyl acetate and washed once with 5 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate. After filtration, the solvent is removed on a rotary evaporator. The residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 400:1→60:1). This gives a light-brown solid.

Workup

  1. concentrationAfter concentration
  2. customon a rotary evaporator
  3. washwashed once with 5 ml of sat. aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is removed on a rotary evaporator
  7. customThe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: cyclohexane/ethyl acetate 400:1→60:1)
  8. customThis gives a light-brown solid

Sources & evidence

ORD record
ord-1ec3d43bd9884c5e88f1b017a787218f
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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