1,3-Dichloroacetone → 2-(4-Bromophenyl)-4-(chloromethyl)oxazole

HRID 1445746Notes

Reaction equation

HRID 1445746 reaction equation
[Br: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>C(O)(C)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:15]=[C:13]([CH2:12][Cl:11])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 696834-Bromobenzamide

Product 1

HCID 155551142-(4-Bromophenyl)-4-(chloromethyl)oxazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-bromo-benzamide (4.03 g, 20.11 mmol), and 1,3-dichloro-acetone (3.83 g, 30.17 mmol) are placed in a 250 mL flask and dissolved in 150 mL of isopropyl alcohol. The mixture is heated to reflux for 5 hours and cooled to ambient temperature. The reaction is concentrated to dryness. The resulting solid is triturated with diethyl ether and filtered to remove unreacted 4-bromo-benzamide. The filtrate is concentrated to the title compound as an oily solid (3.1 g) and is used without further purification. MS (m/e) 273.9 (M+1)

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction is concentrated to dryness
  4. customThe resulting solid is triturated with diethyl ether
  5. filtrationfiltered
  6. customto remove unreacted 4-bromo-benzamide
  7. concentrationThe filtrate is concentrated to the title compound as an oily solid (3.1 g)
  8. customis used without further purification

Sources & evidence

ORD record
ord-5058df3adc024cd0864adfce0d95c7ab
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…