Hydrochloric Acid → 4,4,10,10-Tetramethyl-7-[(2-nitro-1H-imidazol-1-yl)methyl]-8-oxa-5,9-diazapentadecane-3,11-dione dioxime

HRID 975622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975622
Cl[C:2]([CH3:9])([CH3:8])[CH:3]([N:6]=[O:7])[CH2:4][CH3:5].Cl.Cl.Cl.[NH2:13][CH2:14][CH:15]([O:25][NH:26][C:27]([CH3:36])([C:29](=[N:34][OH:35])[CH2:30][CH2:31][CH2:32][CH3:33])[CH3:28])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[N+:22]([O-:24])=[O:23].C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:8][C:2]([CH3:9])([NH:13][CH2:14][CH:15]([CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[N+:22]([O-:24])=[O:23])[O:25][NH:26][C:27]([CH3:28])([CH3:36])[C:29](=[N:34][OH:35])[CH2:30][CH2:31][CH2:32][CH3:33])[C:3](=[N:6][OH:7])[CH2:4][CH3:5]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 122253792-Chloro-2-methyl-3-nitrosopentaneHCID 867504532-[(1-(Aminomethyl)-2-(2-nitro-1H-imidazol-1-yl)ethoxy]amino]-2-methyl-3-heptanone oxime dihydrochloride

Produkt 1

HCID 867504524,4,10,10-Tetramethyl-7-[(2-nitro-1H-imidazol-1-yl)methyl]-8-oxa-5,9-diazapentadecane-3,11-dione dioxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

4-Chloro-4-methyl-3-nitrosopentane (0.52 g, 3.5 mmol, Example 27(A)) was added to a mixture of the hydrochloride title product of step B above (0.62 g, 1.5 mmol) and diisopropylethylamine (0.45 g, 3.5 mmol) in acetonitrile (10 mL), and the mixture was stirred at room temperature for 12 hrs. Acetonitrile was removed on a rotary evaporator and the thick oil obtained was basified with potassium carbonate solution. The light green oil obtained was extracted with ethyl acetate and dried (Na2SO4). Ethyl acetate was removed on a rotary evaporator and the oil obtained was purified by column chromatography (silica gel, ethyl acetate:hexane, 6:4). Fractions containing the product were collected and evaporated to give a colorless oil, which was dried under vacuum to afford a foamy solid. The solid obtained was dissolved in acetonitrile and left at room temperature for 2 hrs. The solid that formed was filtered and recrystallized from acetonitrile.

Aufarbeitung

  1. customAcetonitrile was removed on a rotary evaporator
  2. customthe thick oil obtained
  3. customThe light green oil obtained
  4. extractionwas extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. customEthyl acetate was removed on a rotary evaporator
  7. customthe oil obtained
  8. customwas purified by column chromatography (silica gel, ethyl acetate:hexane, 6:4)
  9. additionFractions containing the product
  10. customwere collected
  11. customevaporated
  12. customto give a colorless oil, which
  13. customwas dried under vacuum
  14. customto afford a foamy solid
  15. customThe solid obtained
  16. waitleft at room temperature for 2 hrs
  17. customThe solid that formed
  18. filtrationwas filtered
  19. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-d6f61557a2634769914f7d2958c9f716
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05608110

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