Sodium Dithionite → 3-Amino-4-(2,5-dichlorophenoxy)benzonitrile

HRID 1946848

Reaktionsgleichung

Reaktionsgleichung von HRID 1946848
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:3]=1[O:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[NH2:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[O:4][C:3]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:2]=1[Cl:1])[C:9]#[N:10]

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 595489424-(2,5-Dichlorophenoxy)-3-nitrobenzonitrile

Produkt 1

HCID 435182193-Amino-4-(2,5-dichlorophenoxy)benzonitrileAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The coupled product 34 was reduced with sodium hydrosulfite ((49.76 g, 268.56 mmol) in a mixture of THF (200 mL) and water (100 mL). After the reaction was complete, THF was removed in vacuo. The product was precipitated out from the remaining reaction mixture, and was collected via vacuum filtration to yield compound 35 (12.961 g, 103.7% yield, 97.3% pure). 1H NMR (500 MHz, DMSO-d6): δ 7.64 (d, J=9 Hz, 1H), 7.31 (dd, J1=9 Hz, J2=2 Hz, 1H), 7.13 (d, J=2 Hz, 1H), 7.08 (d, J=2 Hz, 1H), 6.93 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.74 (d, J=8 Hz, 1H), 5.63 (s, 2H).

Aufarbeitung

  1. customTHF was removed in vacuo
  2. customThe product was precipitated out from the remaining reaction mixture
  3. filtrationwas collected via vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-a93c0b4c1d0f40f3a7e155e3a649ee78
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399456B2

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