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

HRID 1873584Notes

Reaction equation

HRID 1873584 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-dichloroacetone are stirred at 130° C. for 2 days, resulting in the formation of a melt. 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 suspension obtained is poured into 20 ml of ice-water and stirred at RT overnight. The precipitate formed is filtered off and dried in a vacuum drying cabinet at 40° C. overnight.

Workup

  1. customresulting in the formation of a melt
  2. customThe suspension obtained
  3. stirringstirred at RT overnight
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. customdried in a vacuum
  7. customdrying cabinet at 40° C. overnight

Sources & evidence

ORD record
ord-4d7834d0b5a84d53a6b52fe832abbc2b
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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