Acetamide → 4-(4-Bromophenyl)-2-methyl-1,3-oxazole

HRID 452873Notes

Reaction equation

HRID 452873 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=O)[CH2:7]Br)=[CH:4][CH:3]=1.[C:12]([NH2:15])(=[O:14])[CH3:13]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[N:15]=[C:12]([CH3:13])[O:14][CH:7]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 178AcetamideHCID 74544-Bromophenacyl bromide

Product 1

HCID 128731074-(4-Bromophenyl)-2-methyl-1,3-oxazoleYield 22.5%

Procedure

4-Bromophenacyl bromide (21.3 g) and acetamide (11.3 g) were heated together at 130° C. under argon. After 2.5 h the reaction mixture was allowed to cool, and partitioned between water (150 ml) and Et2O (150 ml). The organic phase was washed with aqueous NaOH (0.5N), aqueous HCl (0.5M) and saturated aqueous NaCl solution (100 ml of each), dried (MgSO4) and evaporated to give a brown solid which was recrystallised from hexanes to give the title compound (D14) as an orange solid (4.1 g). LCMS electrospray (+ve) 239 (MH+).

Workup

  1. temperatureto cool
  2. custompartitioned between water (150 ml) and Et2O (150 ml)
  3. washThe organic phase was washed with aqueous NaOH (0.5N), aqueous HCl (0.5M) and saturated aqueous NaCl solution (100 ml of each),
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give a brown solid which
  7. customwas recrystallised from hexanes

Sources & evidence

ORD record
ord-ca041f5bd11a422190a1eca628cc90df
Source dataset
uspto-grants-2013_07
Patent number
US08492375B2

Reaction notes

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