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1-Propanol → HCID 178504130, Verbindung

HRID 1094036
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1094036
N=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[NH:8][C:9]([N:11]1C=CN=C1)=[S:10].Cl[CH2:17][C:18]1[N:19](C)[CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1.[CH2:30](O)CC>>[CH3:30][SH:10]([CH2:17][C:18]1[NH:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:22]=1)[C:9]1[N:11]=[C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][N:3]2[N:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 3

HCID 10311-PropanolHCID 15334493Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amideHCID 591512282-Chloromethyl-1-methyl-4-phenyl-1H-imidazole

Produkt 1

HCID 178504130HCID 178504130, VerbindungAusbeute 62 %

Versuchsvorschrift

An adaptation of the method described in WO 96/01826 was used. Imidazole-1-carbothioic acid (2-imino-2H-pyridin-1-yl)-amide (200 mg, 1.37 mmol) and 2-chloromethyl-1-methyl-4-phenyl-1H-imidazole 6 (300 mg, 1.46 mmol) were dissolved in 1-propanol (25 mL) and the mixture was heated to reflux for 2 hours. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with water and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by chromatography on silica gel to afford the title compound (273 mg, 62%) as a yellow solid. LC-MS: m/z=322.1 (MH+), tR=2.29 min, method B.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue dissolved in dichloromethane
  5. washThe solution was washed with water
  6. dry with materialthe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-aba08010db5c4ddfbd714fdf60dbf3bc
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08133897B2

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