Cyclobutylamine → 3-(Benzo[1,3]dioxol-5-ylamino)-3-cyclobutylamino-2-(4-chlorophenylsulfonyl)-propenenitrile

HRID 840227

Reaktionsgleichung

Reaktionsgleichung von HRID 840227
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11](SC)=[C:12]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:13]#[N:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH:27]1([NH2:31])[CH2:30][CH2:29][CH2:28]1>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([NH:31][CH:27]3[CH2:30][CH2:29][CH2:28]3)=[C:12]([S:15]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:13]#[N:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Komponenten

3

Edukt 2

HCID 75645CyclobutylamineHCID 70149709Benzo[1,3]dioxol-5-ylamino-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile

Produkt 1

HCID 701495213-(Benzo[1,3]dioxol-5-ylamino)-3-cyclobutylamino-2-(4-chlorophenylsulfonyl)-propenenitrileAusbeute 29,1 %

Versuchsvorschrift

3-(Benzo[1,3]dioxol-5-ylamino-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.29 g, 0.7 mmol) was stirred in cyclobutylamine (0.6 ml 7.0 mmol) for 17 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue was crystallised from ethyl acetate to give 88 mg (29%) of the title compound. Mp 189.5° C. 1H NMR (200 MHz, CDCl3): δ=1.6 (m, 2H), 1.75 (m, 2H), 2.05 (m, 2H), 3.80 (m, 1H), 6.02 (s, 2H), 6.5 (m, 2H), 6.79 (d, 2H), 7.50 (dt, 2H), 7.83 (dt, 2H). Analysis: calc. for C20H18ClN3O4S: C, 55.62%; H, 4.20%; N, 9.73%; Found: C, 55.59%; H, 4.21%; N, 9.59%.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was crystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d2468555a8304150adb9a94aaa54dfbf
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06365609B1

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