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Dimethylformamide → HCID 131718228, Verbindung

HRID 1656446
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1656446
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=N.C[N:14](C=O)C.[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1>CN(C1C=CC=CN=1)C.N1C=CC=CC=1>[NH2:14][N:9]=[CH:7][C:6]1[CH:5]=[C:4]([NH:3][CH:21]([CH:22]=[O:23])[CH2:20][CH2:19][C:18]([OH:24])=[O:25])[CH:12]=[CH:11][CH:10]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 7940Glutaric anhydrideHCID 3084651m-Aminobenzamidine dihydrochloride

Produkt 1

HCID 131718228HCID 131718228, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 218852-DimethylaminopyridineKatalysator
HCID 1049
Pyridine
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-Aminobenzamidine di-HCL (5 g, 24 mmol) was added to dry DMF (30 mL). To this solution dry pyridine (5 mL) and glutaric anhydride (3.0 g, 26 mmol), followed by 10 mg dimethylaminopyridine (DMAP) were added. The product was heated for 3 h at 100° C. and allowed to stir at room temperature for 16 h. Solvents were removed in vacuo, water was added to the residue and the pH was brought to a value of 6.8 using dilute sodium hydroxide. An abundant precipitate was filtered, washed with water followed by ethyl acetate. The white solid was filtered and dried in a desiccator to give 5.4 g, 90% of product as a white solid: 1H NMR (d6 -DMSO) δ 1.8 (m, 2H), 2.3 (m, 2H), 2.45 (m, 2H), 7.6 (d, 1H, J=8 Hz), 7.55 (dd, 1H, J=8 Hz and J= 7.5 Hz), 7.85 (d, 1H, J=7.5 Hz), 8.05 (s, 1H), 9.05 (bs, 2H), 9.25 (bs, 2H), 10.4 (s, 1H); MS (FAB) m/e 250.1 (MH+).

Aufarbeitung

  1. additionwere added
  2. customSolvents were removed in vacuo, water
  3. additionwas added to the residue
  4. filtrationAn abundant precipitate was filtered
  5. washwashed with water
  6. filtrationThe white solid was filtered
  7. customdried in a desiccator

Quellen und Nachweise

ORD-Eintrag
ord-7ee2fe3b36b54da783dc9ea5a6ff82c6
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05254573

Notizen zur Reaktion

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