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

HRID 242156

Reaction equation

HRID 242156 reaction equation
Cl[CH2:2][C:3]([CH2:5][Cl:6])=O.[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.S(=O)(=O)(O)O>>[Cl:6][CH2:5][C:3]1[N:14]=[C:12]([C:11]2[CH:15]=[CH:16][C:8]([Cl:7])=[CH:9][CH:10]=2)[O:13][CH:2]=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

With stirring, 816 mg (6.43 mmol) of 1,3-dichloroacetone and 1000 mg (6.43 mmol) of p-chlorobenzamide are heated at +135° C. for 1 h. After cooling to RT, 1.6 ml of conc. sulphuric acid are added, and the mixture is stirred at RT for a further 5 min. The entire mixture is then poured onto 50 ml of ice. A precipitate is formed which is filtered off with suction, dried under high vacuum and then purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→5:1).

Workup

  1. stirringthe mixture is stirred at RT for a further 5 min
  2. customA precipitate is formed which
  3. filtrationis filtered off with suction
  4. customdried under high vacuum
  5. custompurified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→5:1)

Sources & evidence

ORD record
ord-23d6600946a840a6b3df329a990a460f
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Linked notes

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