p-Toluenesulfonyl azide → HCID 73213267, Verbindung

HRID 2381784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2381784
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.S([N:28]=[N+:29]=[N-])(C1C=CC(C)=CC=1)(=O)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.[OH-].[Na+]>[N:1]([C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1)=[N+:28]=[N-:29]

Komponenten

6

Edukt 2

HCID 13661p-Toluenesulfonyl azideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Produkt 1

HCID 73213267HCID 73213267, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (1.20 g, 4.86 mmol), tosyl azide (1.91 g, 9.71 mmol) and benzyl trimethylammonium chloride (0.05 g, 0.27 mmol) in dichloromethane (21 mL) and 40% aqueous sodium hydroxide solution (11 mL) was stirred at ambient temperature for 18 h. The reaction mixture was extracted with dichloromethane (100 mL). The separated organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.83 g, 63%): MS (ES−) m/z 272.2 (M−1).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with dichloromethane (100 mL)
  2. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-0fab73d4ddca403b9bd0a223381784e9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258160B2

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