Ammonium Chloride → Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylate

HRID 883995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 883995
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[S:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][C:27]=4[N+:36]([O-])=O)=[CH:21][CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+]>C(O)C.O1CCCC1.O.C(OCC)(=O)C.[Fe]>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][C:26]4[S:30][C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][C:27]=4[NH2:36])=[CH:21][CH:20]=3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 2

HCID 25517Ammonium ChlorideHCID 67040709Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate

Produkt 1

HCID 67040774Ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-aminothiophene-2-carboxylateAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of the product of Example 90C (0.918 g, 1.679 mmol) in ethanol (14 mL) and tetrahydrofuran (14 mL) was treated with iron powder (0.577 g, 10.33 mmol) and a solution of ammonium chloride (0.588 g, 10.99 mmol) in water (7 mL), then refluxed for one hour. The reaction was cooled, diluted with ethyl acetate (100 mL), and washed with water (3×25 mL) and brine (25 mL). The organic extract was dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as a yellow solid (0.698 g, 1.351 mmol, 80%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.27 (t, J=6.99 Hz, 3 H) 4.19-4.36 (m, 3 H) 4.48 (d, J=6.62 Hz, 2 H) 5.56 (s, 2 H) 7.10 (d, J=8.09 Hz, 2 H) 7.28-7.55 (m, 7 H) 7.74 (d, J=7.35 Hz, 2 H) 7.90 (d, J=7.35 Hz, 2 H) 9.73 (s, 1 H); MS (ESI+) m/z 517 (M+H)+, 539 (M+Na)+.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. washwashed with water (3×25 mL) and brine (25 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-5c64e275ade4468e8bab07426fbb4745
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236950B2

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