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

HRID 734341Notes

Reaction equation

HRID 734341 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-oxazole

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 (D37) 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-55bba1c4c74d437eb615c78727c7674f
Source dataset
uspto-grants-2009_09
Patent number
US07592347B2

Reaction notes

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