Triethylamine → 2-Chloro-4,5-diphenyloxazole

HRID 890870Notes

Reaction equation

HRID 890870 reaction equation
[C:1]1([C:7]2[NH:8][C:9](=O)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:9]1[O:10][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1512454,5-Diphenyl-4-oxazolin-2-one

Product 1

HCID 131311622-Chloro-4,5-diphenyloxazole

Procedure

4,5-Diphenyloxazolone from Step 1 (30 g, 0.126 mol), triethylamine (12.8 g, 0.126 mol), and phosphorous oxychloride (96.6 g, 0.63 mol) were stirred at reflux for 4.0 hours. The mixture was concentrated in vacuo, dissolved in ether (250 mL), washed with 1N HCl, brine, and water, dried over MgSO4 and concentrated to a light yellow oil which was used in the next step without further purification or characterization.

Workup

  1. temperatureat reflux for 4.0 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. dissolutiondissolved in ether (250 mL)
  4. washwashed with 1N HCl, brine, and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a light yellow oil which
  7. customwas used in the next step without further purification or characterization

Sources & evidence

ORD record
ord-6438517de1a44d1694e8d12dd7eeeede
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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