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Acetic Acid → HCID 178492000, Verbindung

HRID 1244318
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1244318
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([C:18]1[NH:27][C:21]2=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=[C:20]2[N:19]=1)=[S:17].Br.CC(O)=O.CS(C)=O.[OH-].[NH4+]>C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([C:18]3[NH:27][C:21]4=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=[C:20]4[N:19]=3)[S:17][C:5]=2[C:6]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 178492018HCID 178492018, Verbindung

Produkt 1

HCID 178492000HCID 178492000, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.3 g 5-Methyl-3H-imidazo[4,5-b]pyridine-2-carbothioic acid (2-methoxy-5-morpholin-4-yl-phenyl)-amide (0.8 mmol) was dissolved in ethyl acetate (3 ml), heated to reflux and treated with 0.27 ml HBr in AcOH (5.7M, 1.6 mmol) and 0.067 ml DMSO (0.94 mmol). Stirring at reflux was continued for 2 h. Upon cooling a precipitation formed, which was isolated and dissolved in water (2 ml). The pH was adjusted to 10 with 25% ammonium hydroxide in water. Once again a precipitation formed, which was filtered. The residue on the filter was washed with water and dried in vacuo. One obtained 0.125 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-methyl-3H-imidazo[4,5-b]pyridine (42%) as a yellow solid; M.p.: 200–210° C.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureat reflux
  4. temperatureUpon cooling
  5. customa precipitation
  6. customformed
  7. customwhich was isolated
  8. customOnce again a precipitation
  9. customformed
  10. filtrationwhich was filtered
  11. washThe residue on the filter was washed with water
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ae3b39c27c874c67b567bbd06fafeeb3
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07122545B2

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