2-Butanamine, 3,3-dimethyl- → 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile

HRID 279126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279126
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)SC)[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:26][CH:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:28]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11](=[C:14]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[NH:26][CH:27]([CH3:28])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701506282-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile

Produkt 1

HCID 701503332-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrileAusbeute 25 %

Versuchsvorschrift

2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.6 mmol) was stirred in 2-amino-3,3-dimethylbutane (1 ml) for 48 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue dissolved in dichloromethane, washed twice with 1N aqueous HCl, once with brine, and once with water. The organic phase was dried (sodium sulphate) and concentrated. The residue was trituated with ether to afford a white crystalline substance which was further purified by flash chromatography(SiO2) using heptane/ethyl acetate (1:1) to yield 85 mg(25%) of the title compound. Mp 80-82 ° C. 1H NMR (200 MHz, CDCl3): δ=0.90 (s, 9H), 1.02 (d, 3H), 3.02 (m, 1H), 7.27 (s, 2H), 7.47 (d, 2H), 7.51 (d,2H), 7.81 (d, 2H);

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed twice with 1N aqueous HCl, once with brine
  4. dry with materialThe organic phase was dried (sodium sulphate)
  5. concentrationconcentrated
  6. customto afford a white crystalline substance which
  7. customwas further purified by flash chromatography(SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-6564973660d046d38d3c64ce3fc6378c
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362205B1

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