Sulfuric Acid → 4-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole

HRID 1630714Notes

Reaction equation

HRID 1630714 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O.S(=O)(=O)(O)O>>[Cl:11][CH2:12][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=2)[O:7][CH:15]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 107931,3-DichloroacetoneHCID 120844-Chlorobenzamide

Product 1

HCID 71315274-(Chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole

Procedure

1 g (6.43 mmol) of 4-chlorobenzamide is heated together with 816 mg of 1,3-dichloroacetone (6.43 mmol) at 135° C. for 1 h. The mixture is allowed to cool to RT, 1 ml of conc. sulphuric acid is added and the mixture is stirred for 5 min. The mixture is then poured onto ice, and the precipitate is filtered off with suction (946 mg). This precipitate is purified on 100 g of silica gel by column chromatography using a gradient of cyclohexane/ethyl acetate 20:1 to 5:1.

Workup

  1. additionThe mixture is then poured onto ice
  2. filtrationthe precipitate is filtered off with suction (946 mg)
  3. customThis precipitate is purified on 100 g of silica gel by column chromatography

Sources & evidence

ORD record
ord-51c404bfbe10490fa587dbd519445d72
Source dataset
uspto-grants-2014_07
Patent number
US08791146B2

Reaction notes

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