Acetic Acid → HCID 178491905, compound

HRID 1902870Notes

Reaction equation

HRID 1902870 reaction equation
C([O:8][N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[N:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([O:22][CH3:23])=[CH:17][C:16]=1[Cl:24])C1C=CC=CC=1.C(O)(=O)C.C(Cl)C1C=CC=CC=1>C(O)C.[Pt]=O>[Cl:21][C:20]1[CH:19]=[C:18]([O:22][CH3:23])[CH:17]=[C:16]([Cl:24])[C:15]=1[N:14]=[C:10]1[NH:11][CH2:12][CH2:13][N:9]1[OH:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7503Benzyl ChlorideHCID 178491903HCID 178491903, compound

Product 1

HCID 178491905HCID 178491905, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

44.3 g of 1-(benzyloxy)-2-[(2,6-dichloro-4-methoxyphenyl)imino]imidazoline are dissolved in 350 ml of ethanol and 350 ml of acetic acid and treated with 13.8 ml of benzyl chloride. The mixture is hydrogenated in the presence of 1 g of platinum oxide under normal pressure. After completion of the hydrogen uptake, the catalyst is removed by filtration and the solution is evaporated. The residue is treated with water and washed with ether. The aqueous phase is made alkaline and extracted with ethyl acetate. After drying and evaporating the organic extracts and recrystallization of the residue from ethyl acetate/methanol, there is obtained 2-[(2,6-dichloro-4-methoxyphenyl)imino]-1-hydroxyimidazolidine of melting point 199°-201°.

Workup

  1. customAfter completion of the hydrogen uptake, the catalyst is removed by filtration
  2. customthe solution is evaporated
  3. additionThe residue is treated with water
  4. washwashed with ether
  5. extractionextracted with ethyl acetate
  6. customAfter drying
  7. customevaporating
  8. customthe organic extracts and recrystallization of the residue from ethyl acetate/methanol

Sources & evidence

ORD record
ord-2254b4e03a2a4ccfa4ae54578cf782f3
Source dataset
uspto-grants-1982_12
Patent number
US04366160

Reaction notes

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