4-Bromoaniline → N-(4-Bromophenyl)benzo[d]oxazol-2-amine

HRID 897633Notes

Reaction equation

HRID 897633 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl[C:10]1[O:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1>>[O:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=[C:10]1[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 78074-BromoanilineHCID 119862-Chlorobenzoxazole

Product 1

HCID 1238838N-(4-Bromophenyl)benzo[d]oxazol-2-amineYield 67.8%

Conditions

Temperature
100 °C

Procedure

4-Bromoaniline (3.9 g, 0.0227 mol) was added to a solution of 2-chlorobenzoxazole (1.16 g, 0.00755 mol) in xylenes and the reaction mixture was heated at 100° C. for 2 hours. It was cooled to ambient temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL), the organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in n-heptane and the precipitate collected by filtration and dried to yield N-(1,3-benzoxazol-2-yl)-N-(4-bromophenyl)amine (1.48 g, 0.00512 mol) as a white solid.

Workup

  1. temperatureIt was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. dry with materialthe organic phase was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in n-heptane
  7. filtrationthe precipitate collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-b1a53a11b3cd4cdf8ee60f697eb69d27
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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