Dimethylformamide → HCID 23061758, compound

HRID 350744Notes

Reaction equation

HRID 350744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][CH:12]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.CN(C)[CH:26]=[O:27]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][C:12]=2[CH:26]=[O:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12561455HCID 12561455, compound

Product 1

HCID 23061758HCID 23061758, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-chlorophenyl)-2-phenyloxazole (14.43 g), phosphorus oxychloride (12.97 g), N,N-dimethylformamide (100 mL) was stirred at 90° C. for 1.5 hrs. The reaction mixture was poured into iced water, and the precipitated solid was collected by filtration, washed successively with aqueous sodium hydrogen carbonate solution and water and dried. The obtained crystals were recrystallized from acetone-hexane to give 4-(4-chlorophenyl)-2-phenyl-5-oxazolecarbaldehyde (7.90 g, 49%) as yellow prism crystals.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed successively with aqueous sodium hydrogen carbonate solution and water
  3. customdried
  4. customThe obtained crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-6d25a13e27cd4c2da40af6405dc38b04
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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