5,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile) → 5,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile)

HRID 1405965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405965
[O:1]([CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([N+:38]([O-])=O)=[C:34]([CH:37]=1)[C:35]#[N:36])[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([N+:16]([O-])=O)=[C:12]([CH:15]=1)[C:13]#[N:14]>CC(O)=O.CC(O)C.[Fe]>[O:1]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][C:11]([NH2:16])=[C:12]([CH:15]=1)[C:13]#[N:14])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][C:30]1[C:31]([O:41][CH2:42][CH2:43][O:44][CH3:45])=[CH:32][C:33]([NH2:38])=[C:34]([CH:37]=1)[C:35]#[N:36]

Komponenten

5

Edukt 1

HCID 867011935,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))-bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile)

Produkt 1

HCID 867011925,5'-((((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile)Ausbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a solution of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(4-(2-methoxyethoxy)-2-nitrobenzonitrile) (0.2 g) in AcOH (10 mL) and i-PrOH (10 mL) was added iron powder (0.5 g). The resulting mixture was heated to reflux for 1 h. After reaction finished, the mixture was cooled to room temperature, filtered, the precipitate washed with EA (10 mL). The combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography to give 0.15 g of 5,5′-((((oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl))bis(oxy))bis(2-amino-4-(2-methoxyethoxy)benzonitrile). 1H-NMR (400 MHz, CDCl3): δ: 6.90 (s, 2H), 6.25 (s, 2H), 4.20-4.16 (br, 4H), 4.15-4.02 (m, 8H), 3.82-3.79 (m, 4H), 3.77-3.75 (m, 4H), 3.72-3.70 (m, 4H), 3.68-3.66 (m, 4H), 3.43 (s, 6H).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. customAfter reaction
  4. filtrationfiltered
  5. washthe precipitate washed with EA (10 mL)
  6. concentrationThe combined washings and filtrate were concentrated under reduced pressure and purification by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d9f497a922f644fe855f1670e2c953a4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916572B2

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