Hydrochloric Acid → HCID 19863774, compound

HRID 1165064Notes

Reaction equation

HRID 1165064 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]2[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[C:26]([OH:33])=[C:25]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:24]=2)=[CH:18][CH:17]=1)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:38].C(NC1C=CC(NC2C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=2)=CC=1)(=O)C1C=CC=CC=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>C1COCC1.O.C(OCC)C.C(OCC)(=O)C>[ClH:38].[ClH:38].[CH2:7]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23]2[CH:28]=[C:27]([C:29]([CH3:30])([CH3:31])[CH3:32])[C:26]([OH:33])=[C:25]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:24]=2)=[CH:20][CH:21]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 14649927HCID 14649927, compoundHCID 19863772HCID 19863772, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19863774HCID 19863774, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 466 mg of LiAlH4 in 30 ml of THF was added a solution of 1.7 g of 4-(4-benzoylaminophenylamino)-2,6-di-tert-butylphenol (free base of Compound 53) in 30 ml of THF, and the mixture was refluxed for 5.5 hours. After cooling, a solution of 15 g of Na2S2O4 in 60 ml of water was added to the reaction mixture, and the resulting mixture was stirred at room temperature for 10 minutes. Then water was added thereto and the mixture was extracted with diethyl ether. The organic layer was dried over MgSO4 and concentrated. The oil thus obtained was dissolved in a small amount of diethyl ether. To this solution was added 2 ml of a solution of 4N hydrogen chloride in ethyl acetate, and the crystals thus precipitated were filtered and recrystallized from isopropanol-diethyl ether, giving 450 mg of the title compound as white crystals.

Workup

  1. temperaturethe mixture was refluxed for 5.5 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe oil thus obtained
  7. customthe crystals thus precipitated
  8. filtrationwere filtered
  9. customrecrystallized from isopropanol-diethyl ether

Sources & evidence

ORD record
ord-07dc6297d7964c47bb4f59cbf7c127b0
Source dataset
uspto-grants-1990_03
Patent number
US04906662

Reaction notes

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