Thionyl Chloride → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 615927Notes

Reaction equation

HRID 615927 reaction equation
[CH3:1][C:2]([NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)([CH3:5])[CH2:3]O.S(Cl)(Cl)=O>C(OCC)C>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]2[O:15][CH2:3][C:2]([CH3:1])([CH3:5])[N:6]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 319320NSC263142

Product 1

HCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleYield 78.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the title compound of Example 2 (0.1 moles) was added dropwise, in the cold, thionyl chloride (0.4 moles) over 35 min. After stirring for one hour, the reaction was transferred to an addition funnel and added dropwise to rapidly stirring diethyl ether (700 ml). After stirring for 20 hours, the white solid was filtered under reduced pressure was washed well with diethyl ether. The dry solid was treated with 20% sodium hydroxide (75 ml). After stirring for 30 minutes the product was extracted into diethyl ether, and the aqueous layer was washed with ether. The combined ether extracts were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to an oil. The oil was distilled under vacuum to yield 20.0 g of the title compound as a colorless liquid, b.p. 69°-73° C./0.04 mm Hg.

Workup

  1. customthe reaction was transferred to an addition funnel
  2. stirringAfter stirring for 20 hours
  3. filtrationthe white solid was filtered under reduced pressure
  4. washwas washed well with diethyl ether
  5. additionThe dry solid was treated with 20% sodium hydroxide (75 ml)
  6. stirringAfter stirring for 30 minutes the product
  7. extractionwas extracted into diethyl ether
  8. washthe aqueous layer was washed with ether
  9. washThe combined ether extracts were washed with water
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure to an oil
  13. distillationThe oil was distilled under vacuum

Sources & evidence

ORD record
ord-d102fef223d040e697773f68fe6944a5
Source dataset
uspto-grants-1985_02
Patent number
US04501895

Reaction notes

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