Hydrochloric Acid → HCID 12898198, compound

HRID 894308Notes

Reaction equation

HRID 894308 reaction equation
[C:1]12([C:14](=S)[NH:13][C:12](=O)[NH:11]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][CH2:3][CH2:2]2.[Na].Cl.[OH-:19].[K+]>O.C(OCC)C.C(O)CC(C)C>[C:1]12([C:14](=[O:19])[NH:13][CH2:12][NH:11]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:4][CH2:3][CH2:2]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 20575272HCID 20575272, compound

Product 1

HCID 12898198HCID 12898198, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 31260Isoamyl AlcoholSolvent

Procedure

In a flame-dried reaction flask containing 10 ml. of freshly distilled isoamyl alcohol, there were placed 300 mg. (0.00129 mole) of 3',4'-dihydro-spiro-[imidazolidine-4,1'(2'H)naphthalene]-2-one-5-thione (prepared as described above) while the entire system was under a dry nitrogen atmosphere. The resulting solution was then treated with 0.5 g. of sodium, which was added in small portions, and the mixture so obtained was heated at 90°-100° C. for a period of 30 minutes. After cooling to room temperature (~25° C.), the excess sodium was destroyed with 10 ml. of methanol and the spent reaction mixture was diluted with water and subsequently extracted with three separate fresh portions of benzene. The combined benzene layers were then washed with water, dried over anhydrous magnesium sulfate and filtered. The resulting filtrate was thereafter evaporated to near dryness while under reduced pressure and the residue so obtained was slurried with diethyl ether and 1 N hydrochloric acid, followed by basification of the aqueous layer with 4 N aqueous potassium hydroxide. Extraction of the latter basified solution with methylene chloride then gave a clear organic extract, which was subsequently washed with water and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there was finally obtained 78 mg. (30%) of crude 3',4'-dihydro-spiro-[imidazolidine-4,1'(2'H)naphthalene]-5-one as the desired final product. Recrystallization of the latter material from ethanol then gave analytically pure 3',4'-dihydro-spiro-[imidazolidine-4,1'(2'H)naphthalene]-5-one, m.p. 181°-183° C.

Workup

  1. customIn a flame-dried reaction flask
  2. additioncontaining 10 ml
  3. additionThe resulting solution was then treated with 0.5 g
  4. customthe mixture so obtained
  5. temperaturewas heated at 90°-100° C. for a period of 30 minutes
  6. customthe excess sodium was destroyed with 10 ml
  7. customof methanol and the spent reaction mixture
  8. extractionsubsequently extracted with three
  9. customseparate fresh portions of benzene
  10. washThe combined benzene layers were then washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customThe resulting filtrate was thereafter evaporated
  14. customthe residue so obtained
  15. extractionExtraction of the latter basified solution with methylene chloride
  16. customthen gave a clear organic extract, which
  17. washwas subsequently washed with water
  18. dry with materialdried over anhydrous magnesium sulfate
  19. customAfter removal of the drying agent
  20. filtrationby means of filtration
  21. customthe solvent by means of evaporation under reduced pressure, there
  22. customRecrystallization of the latter material from ethanol

Sources & evidence

ORD record
ord-ee5a6655fc8b494b93147d8efe2d4c23
Source dataset
uspto-grants-1981_08
Patent number
US04283409

Reaction notes

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