4-Tert-Butylaniline → HCID 2111998, Verbindung

HRID 736372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 736372
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

Komponenten

5

Edukt 3

HCID 698614-Tert-ButylanilineHCID 801724-Cyanobenzoyl chlorideHCID 81531Diisopropylethylamine

Produkt 1

HCID 2111998HCID 2111998, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-cyanobenzoyl chloride (2 g, 12.08 mmol), DIEA (7.3 mL, 42 mmol), and 4-tert-butylaniline (1.9 mL, 11.9 mmol) were stirred in tetrahydrofuran (50 mL) overnight at room temperature. The tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate. The ethyl acetate was washed with H2O and brine, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to afford the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.08-8.12 (m, 2H), 8.01-8.04 (m, 2H), 7.66-7.69 (m, 2H), 7.37-7.41 (m, 2H), 1.28 (s, 9H); MS (ESI+) m/z 279 (M+H)+.

Aufarbeitung

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. washThe ethyl acetate was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-32e45f698db047d4b8425cb819d8b26a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07595332B2

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