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

HRID 242157Notes

Reaction equation

HRID 242157 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[F:17])[C:11]([NH2:13])=[O:12].S(=O)(=O)(O)O>>[Cl:1][CH2:2][C:3]1[N:13]=[C:11]([C:10]2[CH:14]=[CH:15][C:16]([F:17])=[C:8]([F:7])[CH:9]=2)[O:12][CH:5]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 107931,3-DichloroacetoneHCID 5228323,4-Difluorobenzamide

Product 1

HCID 509894234-(Chloromethyl)-2-(3,4-difluorophenyl)-1,3-oxazole

Procedure

With stirring, 500 mg (3.94 mmol) of 1,3-dichloroacetone and 619 mg (3.94 mmol) of 3,4-difluorobenzamide are heated at +135° C. for 1 h. After cooling to RT, the mixture is allowed to stand at this temperature for 90 min 1.0 ml of conc. sulphuric acid is then added, and the mixture is stirred at RT for a further 15 min. The entire mixture is then poured onto 50 ml of ice. Initially, a viscous oil is formed. The mixture is stirred for 60 min, during which time a precipitate is formed which is filtered off with suction, dried under high vacuum and then purified chromatographically on silica gel 60 (mobile phase: isohexane/ethyl acetate 10:1).

Workup

  1. stirringthe mixture is stirred at RT for a further 15 min
  2. customInitially, a viscous oil is formed
  3. stirringThe mixture is stirred for 60 min, during which time a precipitate
  4. customis formed which
  5. filtrationis filtered off with suction
  6. customdried under high vacuum
  7. custompurified chromatographically on silica gel 60 (mobile phase: isohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-282074a588984a62bfbcf31747bfaa56
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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