Methanol → HCID 178426127, compound

HRID 2057948Notes

Reaction equation

HRID 2057948 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]=[C:13]1[NH:17][CH2:16][CH2:15][NH:14]1.CO.[H][H]>[Ni].O1CCCC1>[NH2:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:12]=[C:13]2[NH:17][CH2:16][CH2:15][NH:14]2)[CH:4]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 178418361HCID 178418361, compoundHCID 178426128HCID 178426128, compound

Product 1

HCID 178426127HCID 178426127, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

25.4 gm (0.10 mol) of 2-(2-chloro-4-methyl-5-nitro-phenylimino)-imidazolidine were hydrogenated in a shaker autoclave at 25° to 30° C. and atmospheric pressure in the presence of Raney nickel and in a 1:1 mixture of methanol and tetrahydrofuran until the theoretical amount of hydrogen had been absorbed. Thereafter, the catalyst was separated by suction filtration, and the filtrate was evaporated to dryness in vacuo. The residue was dissolved in 2 N hydrochloric acid, and the solution was extracted with ether; the ether extracts were discarded. The aqueous phase was fractionally extracted with ether at stepwisely increasing pH-values (alkalization with 2 N NaOH), and the uniform fractions were combined, dried over magnesium sulfate and filtered. The ether was removed from the filtrate in vacuo until the weight of the residue remained constant, leaving 6.85 gm (30.5% of theory) of 2-(5-amino-2-chloro-4-methylphenylimino)-imidazolidine, m.p. 155°-157° C., Rf -value 0.70 in the mobile phase 70 parts ethyl acetate, 50 parts isopropanol, 20 parts concentrated ammonium hydroxide; carrier: silicagel G; detector: ultraviolet light and potassium iodoplatinate.

Workup

  1. customwere hydrogenated in a shaker autoclave at 25° to 30° C.
  2. customhad been absorbed
  3. customThereafter, the catalyst was separated by suction filtration
  4. customthe filtrate was evaporated to dryness in vacuo
  5. dissolutionThe residue was dissolved in 2 N hydrochloric acid
  6. extractionthe solution was extracted with ether
  7. extractionThe aqueous phase was fractionally extracted with ether at stepwisely increasing pH-values (alkalization with 2 N NaOH)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe ether was removed from the filtrate in vacuo until the weight of the residue

Sources & evidence

ORD record
ord-7218a4a05e824ca9a67643b8eeccfb9e
Source dataset
uspto-grants-1980_07
Patent number
US04213995

Reaction notes

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