Hydrochloric Acid → HCID 178526276, compound

HRID 1981082Notes

Reaction equation

HRID 1981082 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][CH:18]=[CH:17][C:16]=1[Cl:22])C1C=CC=CC=1.Cl.[H][H]>[Pd].C(O)C>[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[N:14]=[C:10]1[NH:11][CH2:12][CH2:13][N:9]1[OH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178478106HCID 178478106, compound

Product 1

HCID 178526276HCID 178526276, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.34 g. of 1-benzyloxy-2-[(2,6-dichlorophenyl)-imino]imidazolidine is hydrogenated under normal pressure in 5 ml. of ethanol and 2 ml. of 1N hydrochloric acid in the presence of 0.05 g. of palladium-on-charcoal (5%). After the uptake of hydrogen has ended, the catalyst is filtered off and the solution is evaporated. The residue is dissolved in water and the solution is adjusted to pH 10 with caustic soda solution and extracted, first with methylene chloride and then with ethyl acetate. The organic extracts are dried over sodium sulfate and evaporated to dryness in vacuo. The residue is recrystallized from acetonitrile, whereupon 2-[(2,6-dichlorophenyl)imino]-1-hydroxyimidazolidine, m.p. 196°, is obtained. Recrystallization from methanol/acetonitrile raises the melting point to 215°.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe solution is evaporated
  3. dissolutionThe residue is dissolved in water
  4. extractionextracted, first with methylene chloride
  5. dry with materialThe organic extracts are dried over sodium sulfate
  6. customevaporated to dryness in vacuo
  7. customThe residue is recrystallized from acetonitrile, whereupon 2-[(2,6-dichlorophenyl)imino]-1-hydroxyimidazolidine, m.p. 196°
  8. customis obtained
  9. customRecrystallization from methanol/acetonitrile
  10. temperatureraises the melting point to 215°

Sources & evidence

ORD record
ord-6a5487d3f1004893b6977e0661477461
Source dataset
uspto-grants-1985_04
Patent number
US04511720

Reaction notes

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