Phosphorus oxychloride → HCID 20080541, compound

HRID 1653813Notes

Reaction equation

HRID 1653813 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH:9]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[NH:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:9]2[N:10]=[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][Br:17])[O:26][C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20080527HCID 20080527, compound

Product 1

HCID 20080541HCID 20080541, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

4,5-Bis(4-chlorophenyl)-2-(5-bromopentyl)oxazole is prepared in the following manner: 39.5 g of 1,2-bis(4-chlorophenyl)-2-(6-bromohexanamido)ethanone in 80 cm3 of toluene containing 40 g of phosphorus oxychloride are stirred for 3 hours at 80° C. After evaporation to dryness under vacuum, 100 cm3 of ice-cold water are added. The mixture is extracted with diethyl ether (3 times 120 cm3) and the ethereal solutions are washed successively with water (3 times 50 cm3) and saturated aqueous sodium bicarbonate solution (twice 100 cm3). The organic phase is dried and concentrated to dryness. The solid residue is dissolved in 400 cm3 of hexane, the solution is treated with animal charcoal and filtered through kieselguhr, the filtrate is cooled to 10° C. and the precipate is drained and dried. 33 g (87%) of 4,5-bis(4-chlorophenyl)-2-(5-bromopentyl)oxazole are obtained in the form of white crystals, melting point 98° C.

Workup

  1. custom4,5-Bis(4-chlorophenyl)-2-(5-bromopentyl)oxazole is prepared in the following manner
  2. customAfter evaporation to dryness under vacuum, 100 cm3 of ice-cold water
  3. additionare added
  4. extractionThe mixture is extracted with diethyl ether (3 times 120 cm3)
  5. washthe ethereal solutions are washed successively with water (3 times 50 cm3) and saturated aqueous sodium bicarbonate solution (twice 100 cm3)
  6. customThe organic phase is dried
  7. concentrationconcentrated to dryness
  8. dissolutionThe solid residue is dissolved in 400 cm3 of hexane
  9. additionthe solution is treated with animal charcoal
  10. filtrationfiltered through kieselguhr
  11. customdried

Sources & evidence

ORD record
ord-7603c160e3b64f0781b0f718406a87d4
Source dataset
uspto-grants-1995_04
Patent number
US05403852

Reaction notes

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