Ethyl Acetate → 4-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

HRID 1685664

Reaktionsgleichung

Reaktionsgleichung von HRID 1685664
Br[CH2:2][CH2:3][N:4]([N:13]1[CH:17]=[N:16][N:15]=[CH:14]1)[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.[O:18]([C:26]1[CH:27]=[C:28]([SH:32])[CH:29]=[CH:30][CH:31]=1)[Si](C(C)(C)C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[OH:18][C:26]1[CH:27]=[C:28]([S:32][CH2:2][CH2:3][N:4]([N:13]2[CH:17]=[N:16][N:15]=[CH:14]2)[C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[CH:29]=[CH:30][CH:31]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 219768444-[(2-Bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrileHCID 219768683-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenethiol

Produkt 1

HCID 219769104-{[2-(3-Hydroxy-phenylsulfanyl)-ethyl]-[1,2,4]triazol-4-yl-amino}-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-[(2-Bromo-ethyl)-[1,2,4]triazol-4-yl-amino]-benzonitrile (CAB02148=CAB03031, 146 mg, 0.50 mmol), 3-(tert-butyl-dimethylsiloxy)-thiophenol (240 mg, 1.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) in DMF (10 ml) was stirred for 48 hours at room temperature. The mixture was transferred into a separation funnel and ethyl acetate (50 ml) and water (50 ml) were added. The organic layer was separated, washed with brine (30 ml), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallised from methanol. Yield: 93 mg (55%) colourless crystals (STX512). 1H-NMR (400 MHz, d6-DMSO) δ=3.14 (t, J=7.0 Hz, 2H), 4.02 (t, J=7.0 Hz, 2H), 6.53 (d, J=9.0 Hz, 2H), 6.62 (ddd, J=7.8, 2.0, 0.8 Hz, 1H), 6.70-6.72 (m, 2H), 7.10 (dd, J=7.8, 7.8, 1H), 7.70 (d, J=9.0 Hz, 2H), 8.94 (s, 2H), 9.60 (s, 1H, —OH). 13C-NMR (100 MHz, d6-DMSO) δ=29.53 52.46, 102.38, 112.86, 113.57, 115.36, 119.00, 130.11, 133.94, 135.82, 143.50, 150.71, 157.90, 169.59. LRMS (FAB+): 338.2 (100, [M+H]+). C17H15N5OS (337.4) Calculated: C, 60.52% H, 4.48% N, 20.76%, Found: C, 60.6% H, 4.53% N, 20.8%.

Aufarbeitung

  1. customThe mixture was transferred into a separation funnel
  2. customThe organic layer was separated
  3. washwashed with brine (30 ml)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallised from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5276d23471da4115844b9054ec50d83e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148415B2

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