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

HRID 508153Notes

Reaction equation

HRID 508153 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[CH3:11].[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O.S(=O)(=O)(O)O>>[Cl:12][CH2:13][C:14]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH3:11])[CH:4]=2)[O:7][CH:16]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 107931,3-DichloroacetoneHCID 27745784-Fluoro-3-methylbenzamide

Product 1

HCID 582842534-(Chloromethyl)-2-(4-fluoro-3-methylphenyl)-1,3-oxazole

Procedure

2.00 g (12.80 mmol) of 4-fluoro-3-methylbenzamide and 1.79 g (14.08 mmol) of 1,3-dichloro-acetone are stirred at 130° C. for 2 days. A melt is formed. The mixture is then cooled to RT, 3.0 ml of conc. sulfuric acid are added carefully at this temperature and the mixture is stirred for 15 min. The resulting suspension is poured into 20 ml of ice-water and stirred at RT overnight. The precipitate formed is filtered off and dried at 40° C. in a vacuum drying cabinet overnight.

Workup

  1. customA melt is formed
  2. stirringstirred at RT overnight
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. customdried at 40° C. in a vacuum
  6. customdrying cabinet overnight

Sources & evidence

ORD record
ord-01901bcf48d84da2958c5005252af0f4
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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