Thionyl Chloride → 4-(Chloromethyl)-5-(4-chlorophenyl)-1,3-oxazole

HRID 508165Notes

Reaction equation

HRID 508165 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH2:13]O)=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:13][C:9]1[N:10]=[CH:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 58284362[5-(4-Chlorophenyl)-1,3-oxazol-4-yl]methanol

Product 1

HCID 582842644-(Chloromethyl)-5-(4-chlorophenyl)-1,3-oxazole

Procedure

269 mg (0.77 mmol) of the compound from Example 38A are initially charged in 0.43 ml (5.85 mmol) of thionyl chloride. The reaction mixture is stirred at RT for 12 h, and excess thionyl chloride is then removed under reduced pressure. The residue is taken up in 5 ml of ethyl acetate and washed once with 2 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The product obtained is used without further purification in the subsequent reactions.

Workup

  1. customexcess thionyl chloride is then removed under reduced pressure
  2. washwashed once with 2 ml of sat. aqueous sodium bicarbonate solution
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed on a rotary evaporator
  5. customThe product obtained
  6. customis used without further purification in the subsequent reactions

Sources & evidence

ORD record
ord-73aa8356cf0b45e293dc9bff575be878
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

Loading…