Sulfuric Acid → HCID 178426129, compound

HRID 2057951Notes

Reaction equation

HRID 2057951 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[N:13]=[C:14]1[NH:18][CH2:17][CH2:16][NH:15]1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Cl:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([N+:1]([O-:4])=[O:2])[C:7]=1[N:13]=[C:14]1[NH:15][CH2:16][CH2:17][NH:18]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178426368HCID 178426368, compound

Product 1

HCID 178426129HCID 178426129, compoundYield 0.9%

Procedure

50 gm (0.183 mol) of 2-(2-chloro-4-methyl-phenylimino)-imidazolidine nitrate were slowly added over a period of two hours to 70 ml of concentrated sulfuric acid at 5°-10° C., while slightly cooling with ice and thoroughly stirring and the resulting black solution was stirred for one hour more at 5° C. Thereafter, ice was added, the aqueous mixture was made alkaline with 5 N sodium hydroxide, and the precipitate formed thereby was collected, recrystallized from methanol and separated from the mother liquor by suction filtration. The methanol was distilled out of the filtrate, and the residue was eluted on a silicagel column (mobile phase: 20 parts methanol, 10 parts acetone, 50 parts chloroform). The thin-layer chromatographically uniform fractions were combined and evaporated in vacuo, and the solid residue was dried, yielding 0.4 gm (0.86% of theory) of 2-(2-chloro-4-methyl-6-nitro-phenylimino)-imidazolidine, m.p. 198° C., Rf -value 0.7 in the mobile phase 50 parts benzene, 40 parts dioxane, 5 parts ethanol and 5 parts concentrated ammonium hydroxide; carrier: silicagel G, visualization: ultraviolet light and potassium iodoplatinate.

Workup

  1. temperaturewhile slightly cooling with ice
  2. stirringthe resulting black solution was stirred for one hour more at 5° C
  3. additionThereafter, ice was added
  4. customthe precipitate formed
  5. customthereby was collected
  6. customrecrystallized from methanol
  7. customseparated from the mother liquor by suction filtration
  8. distillationThe methanol was distilled out of the filtrate
  9. washthe residue was eluted on a silicagel column (mobile phase: 20 parts methanol, 10 parts acetone, 50 parts chloroform)
  10. customevaporated in vacuo
  11. customthe solid residue was dried

Sources & evidence

ORD record
ord-dffe952a77f34d23adfacb952e4f7e17
Source dataset
uspto-grants-1980_07
Patent number
US04213995

Reaction notes

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