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Imidazole → 2-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide

HRID 1393854
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1393854
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N1C=CN=C1)(N1C=CN=C1)=O.N1C=CN=C1.[H-].[Na+].[NH2:39][C:40]1[S:41][S:42][C:43](=[S:45])[N:44]=1>O1CCCC1.O>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:39][C:40]2[S:41][S:42][C:43](=[S:45])[N:44]=2)=[O:19])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 795Imidazole2×HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 2735329Xanthane hydrideHCID 123873512-[4-(Octyloxy)phenyl]acetic acid

Produkt 1

HCID 596805052-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide
Ausbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-[4-(Octyloxy)phenyl]acetic acid (0.900 g, 3.40 mmol) was dissolved in tetrahydrofuran (11 ml), and 1,1′-carbonyldiimidazole (0.622 g, 4.09 mmol) was added thereto. The imidazole mixture was stirred for 1 hour at 0° C. Sodium hydride (60% oil suspension 0.136 g, 3.40 mmol) was suspended in tetrahydrofuran (11 ml), and 3-amino-1,2,4-dithiazole-5-thione (0.511 g, 3.40 mmol) was added thereto. After being stirred for 30 minutes at 0° C., the reaction mixture, with the imidazole mixture added thereto, was stirred for 3 hours at 0° C. The mixture, with water added thereto, was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over MgSO4, and then concentrated. The obtained residue was purified by silica gel column chromatography (chloroform), to give 2-[4-(octyloxy)phenyl]-N-(3-thioxo-3H-1,2,4-dithiazol-5-yl)acetoamide (Compound 6) (0.290 g, 21%).

Aufarbeitung

  1. stirringwas stirred for 3 hours at 0° C
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-b5e92dda736a4f58a3e179df992b4852
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07348017B2

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