Hydrochloric Acid → HCID 178426126, compound

HRID 2057949Notes

Reaction equation

HRID 2057949 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][NH:11]1.OO.[ClH:17]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Cl:17])=[CH:4][C:3]=1[N:9]=[C:10]1[NH:11][CH2:12][CH2:13][NH:14]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 178426367HCID 178426367, compound

Product 1

HCID 178426126HCID 178426126, compoundYield 6.35%

Conditions

Temperature
45 °C

Procedure

6.08 gm (0.029 mol) of 2-(2-chloro-4-methyl-phenylimino)-imidazolidine were dissolved in 50 ml of concentrated hydrochloric acid, 200 mgm of ferric chloride were added to the solution, and the mixture was heated to 45° C. while vigorously stirring. 3 ml of 30% hydrogen peroxide were now slowly added dropwise, during which time the temperature of the reaction mixture rose to a maximum of 70° C. As soon as the temperature dropped to 40° C. again, the reaction had gone to completion. The reaction mixture was now admixed with ice, and the aqueous mixture was extracted with ether; the ether extracts were discarded. The aqueous phase was fractionally extracted at stepwisely increasing pH-values (alkalization with 2N NaOH), and the uniform fractions were combined, dried over magnesium sulfate and filtered. The ether was evaporated from the filtrate in vacuo, and the residue was dried, yielding 0.45 gm (6.35% of theory) of 2-(2,5-dichloro-4-methyl-phenylimino)-imidazolidine, m.p. 190°-191° C., Rf -value 0.6 in the mobile phase 50 parts benzene, 40 parts dioxane, 5 parts ethanol, 5 parts concentrated ammonium hydroxide; carrier: silicagel G; detector: potassium iodoplatinate.

Workup

  1. customrose to a maximum of 70° C
  2. additionAs soon as the temperature dropped to 40° C. again
  3. extractionthe aqueous mixture was extracted with ether
  4. extractionThe aqueous phase was fractionally extracted at stepwisely increasing pH-values (alkalization with 2N NaOH)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe ether was evaporated from the filtrate in vacuo
  8. customthe residue was dried

Sources & evidence

ORD record
ord-b21d8819a70644b78aa84d3e611983cd
Source dataset
uspto-grants-1980_07
Patent number
US04213995

Reaction notes

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