Benzoyl isocyanate → Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate

HRID 44395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44395
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:4]([CH3:14])[C:3]=1[C:15]#[N:16].[C:17]([N:25]=[C:26]=[O:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1.CCOC(C)=O>[C:17]([NH:25][C:26](=[O:27])[NH:1][C:2]1[S:6][C:5]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[C:4]([CH3:14])[C:3]=1[C:15]#[N:16])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 2

HCID 78210Benzoyl isocyanateHCID 18445366Tert-butyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate

Produkt 1

HCID 57456933Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylateAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate (example 64b) (16 g, 67.14 mmol) in dioxane (200 mL), was added benzoyl isocyanate (10 g, 67.14 mmol). The reaction mixture was stirred at rt overnight, and upon completion was diluted with EtOAc, washed with NaHCO3, water, brine, dried over MgSO4, filtered and concentrated to yield tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate (21.78 g, 84%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ1.54 (s, 9H), 3.58 (s, 3H), 7.58 (t, J=7.5 Hz, 2H), 7.71 (t, J=7.5 Hz, 1H), 7.88 (d, J=7.5 Hz, 1H), 8.05 (d, J=7.5 Hz, 2H), 12.25 (br s, 1H).

Aufarbeitung

  1. washwashed with NaHCO3, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ead60eac00644ee3a37bc708d3093910
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541421B2

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