Hydrazine → HCID 178486505, Verbindung

HRID 460337

Reaktionsgleichung

Reaktionsgleichung von HRID 460337
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH2:7][CH2:6]2.[Cl:15][C:16]1[CH:17]=[C:18]([N:23]=[C:24]=S)[CH:19]=[C:20]([Cl:22])[CH:21]=1.C[Si](C)(C)[Si](C)(C)C.[Li].[NH2:35][NH2:36]>C(OCC)(=O)C.C(O)(=O)C.C1COCC1>[Cl:15][C:16]1[CH:17]=[C:18]([NH:23][C:24]2[NH:36][N:35]=[C:8]3[C:9]4[C:5]([CH2:6][C:7]=23)=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=4)[CH:19]=[C:20]([Cl:22])[CH:21]=1

Komponenten

8

Edukt 4

HCID 9321HydrazineHCID 750185,6-Dimethoxy-1-indanoneHCID 1387763,5-Dichlorophenyl isothiocyanateHCID 57425481Lithium hexamethyldisilane

Produkt 1

HCID 178486505HCID 178486505, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5,6-dimethoxyindan-1-one, Compound 3a, (4 g, 0.021 mole), 3,5-dichlorophenyl isothiocyanate, Compound 3b, (4.45 g, 0.022 mole) and THF (30 mL) was added to lithium hexamethyldisilane (26.9 mL, 0.269 mole) dropwise at room temperature with stirring. Hydrazine (1.04 mL, 0.032 mole) and acetic acid (1.65 mL) were added to the reaction mixture, which was then stirred at room temperature for 12 hrs. The reaction continued at 75° C. overnight. The resulting organics were first diluted with ethyl acetate (100 mL), then washed with water and brine solution, dried (Na2SO4), and solvent was removed in vacuo. The chemical residues were recrystallized from ethanol. The first and second crops of solid were combined and dissolved in hot CH3CN, to which an equal volume of HCl-ether solution was added to precipitate the title compound (Compound 19), which was collected and dried under vacuum at 60° C. mp>270° C.; MS m/z 376 and 378 (M+H)+; 1HNMR (DMSO-d6): 3.44(s, 2H), 3.83(s, 3H), 3.82(s, 3H),6.93(s, 1H),7.19 (s, 1H), 7.21(s, 1H), 7.35(s, 2H).

Aufarbeitung

  1. stirringwas then stirred at room temperature for 12 hrs
  2. washwashed with water and brine solution
  3. dry with materialdried (Na2SO4), and solvent
  4. customwas removed in vacuo
  5. customThe chemical residues were recrystallized from ethanol
  6. dissolutiondissolved in hot CH3CN, to which an equal volume of HCl-ether solution
  7. additionwas added
  8. customto precipitate the title compound (Compound 19), which
  9. customwas collected
  10. customdried under vacuum at 60° C. mp>270° C.

Quellen und Nachweise

ORD-Eintrag
ord-98d9cb999b3f4aba9250b7907b37240f
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196110B2

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