Phosphorus oxide (P4O10) → 2-(4-Bromophenyl)oxazole

HRID 1597529Notes

Reaction equation

HRID 1597529 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH2:9][CH:10]([O:14]CC)OCC)=O)=[CH:4][CH:3]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])(O)=O.[Na+].[NH4+].[OH-]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:14][CH:10]=[CH:9][N:8]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 14812Phosphorus oxide (P4O10)HCID 14923Ammonium HydroxideHCID 516892Sodium BicarbonateHCID 223168934-bromo-N-(2,2-diethoxyethyl)benzamide

Product 1

HCID 110750322-(4-Bromophenyl)oxazoleYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
180 °C

Procedure

4-Bromo-N-(2,2-diethoxyethyl)benzamide was dissolved in concentrated sulfuric acid at 0° C. To phosphorus pentoxide (5.2 g, 18.3 mmol) was added the sulfuric acid solution, and the mixture was heated at 180° C. for 30 minutes. The reaction mixture was cooled down to room temperature, and poured into ice. The whole was made basic by addition of NaHCO3 and ammonia aqueous solution. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give title compound (1.23 g, 70% yield).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. additionpoured into ice
  3. extractionThe whole was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cefc6875c704ee39362e88a76011311
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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