Sodium Iodide → 5.5'-[[(4-Methoxybenzyl)imino]bis(propane-3,1-diylimino)]bis(2-methyl-1,3-benzothiazole-4,7-dione)

HRID 908673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908673
C(N(C(C)C)CC)(C)C.Br[CH2:11][CH2:12][CH2:13][NH:14][C:15]1[C:24](=[O:25])[C:19]2[N:20]=[C:21]([CH3:23])[S:22][C:18]=2[C:17](=[O:26])[CH:16]=1.[I-].[Na+].[CH3:29][O:30][C:31]1[CH:54]=[CH:53][C:34]([CH2:35][NH:36][CH2:37][CH2:38][CH2:39][NH:40][C:41]2[C:50](=[O:51])[C:45]3[N:46]=[C:47]([CH3:49])[S:48][C:44]=3[C:43](=[O:52])[CH:42]=2)=[CH:33][CH:32]=1>C(#N)C>[CH3:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([CH2:35][N:36]([CH2:37][CH2:38][CH2:39][NH:40][C:41]2[C:50](=[O:51])[C:45]3[N:46]=[C:47]([CH3:49])[S:48][C:44]=3[C:43](=[O:52])[CH:42]=2)[CH2:11][CH2:12][CH2:13][NH:14][C:15]2[C:24](=[O:25])[C:19]3[N:20]=[C:21]([CH3:23])[S:22][C:18]=3[C:17](=[O:26])[CH:16]=2)=[CH:53][CH:54]=1

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 673934555-[(3-Bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dioneHCID 673938865-({3-[(4-Methoxybenzyl)amino]propyl}amino)-2-methyl-1,3-benzothiazole-4,7-dione

Produkt 1

HCID 673928445.5'-[[(4-Methoxybenzyl)imino]bis(propane-3,1-diylimino)]bis(2-methyl-1,3-benzothiazole-4,7-dione)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

22 μl (128 μmol; 2 equivalents) of diisopropylethylamine, 21 mg (64 μmol; 1 equivalent) of 5-[(3-bromopropyl)amino]-2-methyl-1,3-benzothiazole-4,7-dione and a spatula tip's worth of sodium iodide are added to 23.6 mg (64 μmol) of 5-({3-[(4-methoxybenzyl)amino]propyl}amino)-2-methyl-1,3-benzothiazole-4,7-dione dissolved in 5 ml of acetonitrile. The reaction mixture is maintained under stirring under microwaves at 165° C. for 15 minutes, then the solvent is evaporated off under reduced pressure and the reaction residue is taken up in dichloromethane, followed by washing with 3 times 50 ml of water. The organic phases are combined, dried over magnesium sulphate and the solvent is evaporated off under reduced pressure. The expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 93/7) and obtained in the form of a red oil.

Aufarbeitung

  1. temperatureThe reaction mixture is maintained
  2. customthe solvent is evaporated off under reduced pressure
  3. washby washing with 3 times 50 ml of water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is evaporated off under reduced pressure
  6. customThe expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol: 93/7)
  7. customobtained in the form of a red oil

Quellen und Nachweise

ORD-Eintrag
ord-c17d9146577c4e928b4f30cb6ecc25a7
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017637B2

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