Thionyl Chloride → Methyl 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole-5-carboxylate

HRID 508171Notes

Reaction equation

HRID 508171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:15]([O:17][CH3:18])=[O:16])=[C:11]([CH2:13]O)[N:12]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>>[Cl:21][CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:9][C:10]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 58284345Methyl 2-(4-chlorophenyl)-4-(hydroxymethyl)-1,3-oxazole-5-carboxylate

Product 1

HCID 58284430Methyl 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole-5-carboxylate

Procedure

100 mg (0.43 mmol) of the compound from Example 44A, together with 0.24 ml (3.24 mmol) of thionyl chloride, are stirred at RT for 8 h. The excess thionyl chloride is removed under reduced pressure and the residue is taken up in about 5 ml of ethyl acetate. The mixture is washed once with 2 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The product obtained is used without further purification in the subsequent reactions.

Workup

  1. customThe excess thionyl chloride is removed under reduced pressure
  2. washThe mixture is washed 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 under reduced pressure
  5. customThe product obtained
  6. customis used without further purification in the subsequent reactions

Sources & evidence

ORD record
ord-6b7e7f26f04c47f5abd74893c73ab4d4
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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