HCID 68138655, compound → HCID 68138838, compound

HRID 1658526Notes

Reaction equation

HRID 1658526 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([N:10]1[CH2:14][CH2:13][N:12]=[CH:11]1)[OH:9]>CC(C)=O.O>[N:10]1([C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[O:9])[CH2:14][CH2:13][N:12]=[CH:11]1

Participants

4

Reactant 1

HCID 68138655HCID 68138655, compound

Product 1

HCID 68138838HCID 68138838, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of α-(o-bromophenyl)-2-imidazoline-methanol (16.0 g.) in acetone (600 ml.) and water (150 ml.) was stirred with deactivated precipitated manganese dioxide (100 g.) for 24 hours. [The commerical precipitated manganese dioxide was deactivated by stirring with water for 1 hour. and drying in a vacuum oven at ca.65°-70°C for 5 hours]. After filtering and washing the manganese dioxide with acetone, the solution was evaporated to a small volume under reduced pressure, diluted with water and extracted with chloroform. The combined extracts were dried (MgSO4), the solvent removed and the residue allowed to crystallise from a small volume of ether to yield crude o-bromophenyl 2-imidazolinyl ketone (11.5 g.). A sample recrystallised from benzene petroleum (b.p. 60°-80°) had m.p. 149°-151°. [Found: C, 47.9; H, 3.7; N, 11.1%; C10H9BrN2O requires C, 47.5; H, 3.6; N, 11.1%] .

Workup

  1. customwith deactivated precipitated manganese dioxide (100 g.) for 24 hours
  2. custom[The commerical precipitated manganese dioxide
  3. customand drying in a vacuum oven at ca
  4. wait65°-70°C for 5 hours]
  5. filtrationAfter filtering
  6. washwashing the manganese dioxide with acetone
  7. customthe solution was evaporated to a small volume under reduced pressure
  8. additiondiluted with water
  9. extractionextracted with chloroform
  10. dry with materialThe combined extracts were dried (MgSO4)
  11. customthe solvent removed
  12. customto crystallise from a small volume of ether

Sources & evidence

ORD record
ord-78cb3391be8f471f9abeda8374ef760e
Source dataset
uspto-grants-1976_06
Patent number
US03965112

Reaction notes

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