Bicarbonate Ion → 2-Amino-3-chloro-5-morpholin-4-yl-benzonitrile

HRID 1867284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867284
[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([NH2:11])=[CH:6][C:3]=1[C:4]#[N:5].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.C(N(CC)C(C)C)(C)C.C(=O)(O)[O-]>CN(C)C=O>[NH2:1][C:2]1[C:9]([Cl:10])=[CH:8][C:7]([N:11]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 4

HCID 769Bicarbonate IonHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 137997002,5-Diamino-3-chlorobenzonitrile

Produkt 1

HCID 674078362-Amino-3-chloro-5-morpholin-4-yl-benzonitrileAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

2,5-Diamino-3-chloro-benzonitrile (387 mg), bis-(2-bromoethyl)ether (0.35 mL) and N,N-diisopropyl-ethylamine (1.25 mL) were mixed in N,N-dimethylformamide (4 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. Saturated aqueous bicarbonate (20 mL) was added and the crude mixture was extracted with ethyl acetate (20 mL). The organic phase was washed with water (20 mL) and brine (20 mL), dried over sodium sulfate and concentrated in vacuo to furnish 0.50 g (91%) of the title compound as a brown solid. LC-MS (m/z) 238 (MH+); tR=2.31, (UV, ELSD) 85%, 95%. 1H NMR (500 MHz, DMSO-d6): 2.97 (m, 4H), 3.69 (m, 4H), 5.59 (s, 2H), 7.04 (d, 1H), 7.29 (d, 1H).

Aufarbeitung

  1. extractionthe crude mixture was extracted with ethyl acetate (20 mL)
  2. washThe organic phase was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2f12528e07ce4e6694b3914ed3bb7af5
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632835B2

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