Allyl bromide → HCID 12952488, compound

HRID 2286230Notes

Reaction equation

HRID 2286230 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:4]=1[N:10]([C:12]1[NH:13][CH2:14][CH2:15][N:16]=1)[OH:11].[Na].[CH2:18](Br)[CH:19]=[CH2:20]>C(O)C>[CH2:20]([O:11][N:10]([C:12]1[NH:16][CH2:15][CH2:14][N:13]=1)[C:4]1[C:5]([F:9])=[CH:6][CH:7]=[CH:8][C:3]=1[Br:2])[CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 5360545SodiumHCID 12952479HCID 12952479, compound

Product 1

HCID 12952488HCID 12952488, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.0 gm (0.016 mol) of 2-[N-(2-bromo-6-fluoro-phenyl)-N-hydroxy-amino]-2-imidazoline hydrochloride and 0.7 gm of sodium were dissolved in 75 cc of absolute ethanol, and then 1.6 ml (about 115% of the stoichiometrically required amount) of allyl bromide were added to the solution. The resulting mixture was stirred for one hour at room temperature, and was then evaporated. The residue was dissolved in dilute (about 1 N) hydrochloric acid, and the resulting solution was extracted with ether (the ethereal extracts were discarded). The acidic aqueous phase was then fractionally extracted with ether at stepwisely increasing pH-values (addition of 2-N-sodium hydroxide), and these ethereal extracts were also discarded. The aqueous phase was now made alkaline with 5 N sodium hydroxide, whereupon a white, amorphous substance precipitated, which was collected by suction filtration, washed with water and dried. 2.95 gm (58.3% of theory) of the compound of the formula ##STR4## were obtained. It had a melting point of 141° C.

Workup

  1. customwas then evaporated
  2. dissolutionThe residue was dissolved
  3. additionin dilute (about 1 N) hydrochloric acid
  4. extractionthe resulting solution was extracted with ether (the ethereal extracts
  5. extractionThe acidic aqueous phase was then fractionally extracted with ether at stepwisely increasing pH-values (addition of 2-N-sodium hydroxide)
  6. customwhereupon a white, amorphous substance precipitated
  7. filtrationwhich was collected by suction filtration
  8. washwashed with water
  9. customdried
  10. customwere obtained

Sources & evidence

ORD record
ord-c12e1f1954fd4998a5372bb41dd50ee8
Source dataset
uspto-grants-1982_04
Patent number
US04327106

Reaction notes

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