2-Butanamine, 2-methyl- → 3-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethylpropylamino)-2-methanesulfonyl-2-propenenitrile

HRID 840244

Reaktionsgleichung

Reaktionsgleichung von HRID 840244
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11](SC)=[C:12]([S:15]([CH3:18])(=[O:17])=[O:16])[C:13]#[N:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:21][C:22]([NH2:26])([CH3:25])[CH2:23][CH3:24]>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([NH:26][C:22]([CH3:25])([CH3:21])[CH2:23][CH3:24])=[C:12]([S:15]([CH3:18])(=[O:17])=[O:16])[C:13]#[N:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 689862-Butanamine, 2-methyl-HCID 701495853-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

Produkt 1

HCID 701495753-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethylpropylamino)-2-methanesulfonyl-2-propenenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 3-(benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile(0.800 g, 2.5 mmol) and 1,1-dimethylpropylamine (2.92 ml) in 10 ml of acetonitrile was stirred and refluxed for one week under nitrogen. The reaction mixture was concentrated and the residue dissolved in dichloromethane, washed twice with 1N aqueous HCl, once with brine, and trice with water. The organic phase was dried (sodium sulphate) and evaporated to afford the title compound as white crystals. Mp 86-88° C. 1H NMR (200 MHz, DMSO-d6): δ=0.90 (t, 3H), 1.34 (s, 6H), 1.70 (q, 2H), 3.04 (s, 3H), 6.66 (dd, 1H), 6.74 (d, 1H), 6.88 (d, 1H), 7.21 (s, 1H), 8.19 (s, 1H).

Aufarbeitung

  1. temperaturerefluxed for one week under nitrogen
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue dissolved in dichloromethane
  4. washwashed twice with 1N aqueous HCl, once with brine, and trice with water
  5. dry with materialThe organic phase was dried (sodium sulphate)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9c3ecb90e9ed463f8366cc7494329c93
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365609B1

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