Hydrochloric Acid → HCID 178509798, compound

HRID 1590019Notes

Reaction equation

HRID 1590019 reaction equation
C[O:2][CH:3]=[CH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.Cl>O1CCCC1>[CH:3]([CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=2)[CH2:9][CH2:10]1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178495106HCID 178495106, compound

Product 1

HCID 178509798HCID 178509798, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 1 l capacity three-necked flask were added the compound obtained in the above item (ii) (36.2 g, 0.15 mol), 2N-hydrochloric acid (142 ml) and tetrahydrofuran (560 ml), followed by refluxing these for one hour, distilling off tetrahydrofuran, adding water (100 ml) to extract with ethyl acetate, washing the extract with 1N-NaOH aqueous solution, washing with water till the washing water became neutral, drying over magnesium sulfate, removing magnesium sulfate, concentrating under reduced pressure, recrystallizing from a mixed solvent of heptane with ethyl acetate and drying to obtain white crystals (20.5 g). The NMR spectra of this product accorded with those of the captioned compound.

Workup

  1. additionInto a 1 l capacity three-necked flask were added the compound
  2. temperatureby refluxing these for one hour
  3. distillationdistilling off tetrahydrofuran
  4. additionadding water (100 ml)
  5. extractionto extract with ethyl acetate
  6. washwashing the
  7. extractionextract with 1N-NaOH aqueous solution
  8. washwashing with water till the washing water
  9. dry with materialdrying over magnesium sulfate
  10. customremoving magnesium sulfate
  11. concentrationconcentrating under reduced pressure
  12. customrecrystallizing from a mixed solvent of heptane with ethyl acetate
  13. customdrying

Sources & evidence

ORD record
ord-0427ea5429ff48e39f5efc3ae1268d33
Source dataset
uspto-grants-1993_04
Patent number
US05202055

Reaction notes

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