1-Bromo-3,6-dioxaheptane → 3-(2-(2-Methoxyethoxy)ethylamino)-5-amino-4-chlorobenzonitrile

HRID 921865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 921865
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH2:11])[C:9]=1[Cl:10])[C:5]#[N:6].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19]>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:11][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:9]=1[Cl:10])[C:5]#[N:6]

Komponenten

6

Edukt 2

HCID 1235321-Bromo-3,6-dioxaheptaneHCID 124029953,5-Diamino-4-chlorobenzonitrile

Produkt 1

HCID 899226323-(2-(2-Methoxyethoxy)ethylamino)-5-amino-4-chlorobenzonitrileAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3,5-diamino-4-chlorobenzonitrile (220 mg, 1.313 mmol) in DMF (3 mL) was added IIlunig's Base (2.75 mL, 15.75 mmol) followed by 1-bromo-2-(2-methoxyethoxy)ethane (1442 mg, 7.88 mmol). The resulting solution was heated at 100° C. for 16 h. LC-MS indicated ca. 30% conversion. It was diluted with EtOAc and water. After separating the layers, the aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Purification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g) gave 3-amino-4-chloro-5-((2-(2-methoxyethoxy)ethyl)amino)benzonitrile (100 mg) as an orange oil.

Aufarbeitung

  1. customAfter separating the layers
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g)

Quellen und Nachweise

ORD-Eintrag
ord-bdc587d5c255475392306778bfcbba6d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273057B2

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