2,3-Diaza-spiro[4.4]non-2-ene → HCID 178464598, Verbindung

HRID 1044705

Reaktionsgleichung

Reaktionsgleichung von HRID 1044705
I.[CH2:2]([NH:4][C:5](=[NH:8])SC)[CH3:3].[CH2:9]1[C:13]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:12][N:11]=[N:10]1>N1C=CC=CC=1>[CH2:2]([NH:4][C:5]([N:10]1[N:11]=[CH:12][C:13]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9]1)=[NH:8])[CH3:3]

Komponenten

4

Edukt 2

HCID 547519672,3-Diaza-spiro[4.4]non-2-eneHCID 178464634HCID 178464634, Verbindung

Produkt 1

HCID 178464598HCID 178464598, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

40.89 g 1-Ethyl-2-methyl-isothiourea hydroiodide was dissolved in 150 mL pyridine at 40° C. Subsequently, 20.00 g 2,3-diaza-spiro[4.4]non-2-ene was added and the mixture was stirred overnight under reflux. The mixture was cooled to 60° C. and concentrated under reduced pressure, and the orange residue was taken up in DCM (250 mL). The organic phase was extracted 3 times with water, dried over Na2SO4 and evaporated under reduced pressure. Residual pyridine was removed by azeotropic destillation with water under reduced pressure at 60° C., and residual water was removed by azeotropic destillation with isopropanol under reduced pressure at 60° C. This yielded 31.5 g of a yellow/brown oil containing ˜80% of anticipated product which was used in subsequent steps without further purification. 1H NMR (400 MHz, CDCl3) δ 1.35 (t, J=7.22 Hz, 3H), 1.57-1.99 (m, 8H), 3.60 (q, J=7.22 Hz, 2H), 4.04 (s, 2H), 7.03 (s, 1H) [guanidine NH2 invisible].

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. extractionThe organic phase was extracted 3 times with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customResidual pyridine was removed by azeotropic destillation with water under reduced pressure at 60° C.
  7. customresidual water was removed by azeotropic destillation with isopropanol under reduced pressure at 60° C
  8. additionThis yielded 31.5 g of a yellow/brown oil containing ˜80% of anticipated product which
  9. customwas used in subsequent steps without further purification

Quellen und Nachweise

ORD-Eintrag
ord-39271de79d3f4bbb8bdb297d9e4ce75d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563723B2

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