Allyl bromide → HCID 12884358, compound

HRID 2199066Notes

Reaction equation

HRID 2199066 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][NH:4][C:3]1=[N:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15].[CH2:16](Br)[CH:17]=[CH2:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[N:7]([CH2:18][CH:17]=[CH2:16])[C:8]1[C:9]([Cl:15])=[CH:10][CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 178480594HCID 178480594, compound

Product 1

HCID 12884358HCID 12884358, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 4.9 gm (0.02 mol) of 1-methyl-2-(2,6-dichlorophenyl-imino)-imidazolidine, 2.1 ml of allyl bromide (125% of the stoichiometrically required amount), 2.7 gm of sodium carbonate and 25 ml of ethanol was refluxed for 5.5 hours while stirring. Thereafter, the reaction mixture was filtered, the filtrate was evaporated in vacuo to dryness, the residue was dissolved in dilute (about 1 N) hydrochloric acid, and the resulting solution was extracted with ether (the ethanol extracts were discarded). The acidic aqueous phase was then fractionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide). The thin-layer chromatographically uniform fractions were combined, dried over magnesium sulfate, and the ether was evaporated in vacuo, leaving an oil which crystallized gradually throughout. 2.3 gm (40.5% of theory) of the compound of the formula ##STR7## having a melting point of 59°-61° C. were obtained.

Workup

  1. temperaturewas refluxed for 5.5 hours
  2. filtrationThereafter, the reaction mixture was filtered
  3. customthe filtrate was evaporated in vacuo to dryness
  4. dissolutionthe residue was dissolved
  5. additionin dilute (about 1 N) hydrochloric acid
  6. extractionthe resulting solution was extracted with ether (the ethanol extracts
  7. extractionThe acidic aqueous phase was then fractionally extracted with ether at stepwisely increasing pH-values (addition of 2 N sodium hydroxide)
  8. dry with materialdried over magnesium sulfate
  9. customthe ether was evaporated in vacuo
  10. customleaving an oil which
  11. customcrystallized gradually throughout
  12. customwere obtained

Sources & evidence

ORD record
ord-9d1eafd63bba471ab317a7d4f42b2bf8
Source dataset
uspto-grants-1982_11
Patent number
US04361575

Reaction notes

Loading…