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Sodium Sulfate → HCID 70535708, compound

HRID 1702762
Notes
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Reaction equation

HRID 1702762 reaction equation
[CH2:1]([N:3]1[C:8](=O)[CH2:7][O:6][C@@H:5]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH2:12][CH2:13][CH2:14][C@@H:4]12)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>O1CCCC1.CCOCC.C(O)(C)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[CH2:1]([N:3]1[CH2:8][CH2:7][O:6][C@@H:5]2[C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[CH2:12][CH2:13][CH2:14][C@@H:4]12)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 444266Maleic AcidHCID 21226445Aluminium lithium hydrideHCID 70540935HCID 70540935, compound

Product 1

HCID 70535708HCID 70535708, compound

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Solvent
HCID 3776IsopropanolSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

The 1,4-oxazin-3-one from Step B was dissolved in 50 ml of tetrahydrofuran and added dropwise to 0.3 g (0.008 m) of lithium aluminum hydride in 50 ml of tetrahydrofuran. The mixture was heated at reflux temperature for one hour, cooled and treated with sufficient saturated aqueous sodium sulfate solution to quench excess lithium aluminum hydride. The mixture was filtered and concentrated to dryness in vacuo. The residue was dissolved in methylene chloride, dried (Na2SO4), and concentrated to dryness in vacuo to a residue of crude product (2.1 g, 81%). The maleate salt was prepared by treating with a stoichiometric amount of maleic acid in a minimum of warm isopropanol and adding ether to the cooled solution to incipient cloudiness. After precipitation was complete the salt was collected and recrystallized from benzene to give trans-4-ethyl-2,3,4,4a,5,6,7,11b-octahydrobenzo[6,7]cyclohept[1,2-b]-1,4-oxazine hydrogen maleate, m.p. 132°-135° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for one hour
  3. temperaturecooled
  4. customto quench excess lithium aluminum hydride
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated to dryness in vacuo
  7. dissolutionThe residue was dissolved in methylene chloride
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to dryness in vacuo to a residue of crude product (2.1 g, 81%)
  10. customAfter precipitation
  11. customwas collected
  12. customrecrystallized from benzene

Sources & evidence

ORD record
ord-84637498384941be80fba603719a09bd
Source dataset
uspto-grants-1982_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04349548

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes