Hydrochloric Acid → HCID 66793432, Verbindung

HRID 561948

Reaktionsgleichung

Reaktionsgleichung von HRID 561948
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].Cl.N[CH:18]([CH3:23])[CH2:19][N:20]([CH3:22])[CH3:21].N1C=CN=C1.CCN(CC)CC>O1CCOCC1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[N:6]([CH:18]([CH3:23])[CH2:19][N:20]([CH3:22])[CH3:21])[C:5]2=[O:15]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 8471TriethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

Produkt 1

HCID 66793432HCID 66793432, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 5-amino-6-nitro-isoindole-1,3-dione (1.66 g, 8.0 mmol), HCl salt of 2-amino-N,N-dimethyl-propylamine (5.3 g, crude, <30 mmol), imidazole (1.36 g, 20 mmol) and Et3N (8.4 mL, 6.07 g, 60 mmol) in dioxane (80 mL) was sealed in a ChemGlass heavy wall pressure flask. After it was heated at 130° C. for 72 h, the reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure. The chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (240:10:1) afforded the title compound (1.49 g, 64%). 1H NMR (DMSO-d6) δ 1.32 (d, J=6 Hz, 3H, CH3), 2.09 (s, 6H, 2CH3), 2.25 (m, 1H), 2.95 (m, 1H), 4.35 (m, 1H), 7.43 (s, 1H), 8.29 (s, 1H), 8.39 (br s, 2H, NH). ESI-MS m/z 293.1 (MH+).

Aufarbeitung

  1. customwas sealed in a ChemGlass heavy wall pressure flask
  2. customthe reaction mixture was evaporated to dryness at 95° C. (the bath temperature) under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-05296fc8dc2647c29d34d863fda2fccf
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063225B2

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