Reaktion #2079743

Reaktionsgleichung

4-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

triethylamine

cyanogen bromide

→

title compound

Ausbeute 7.5%

{(2Z)-3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-4,4-dimethyl-1,3-oxazolidin-2-ylidene}cyanamide

Ausbeute 7.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   Sonstigethe tetrahydrofuran was removed in vacuo
3. 3
   SonstigePurification by normal phase HPLC on a phenomenex cyano column
4. 4
   Wascheneluting with hexane/1,2-dimethoxyethane (9:1 to 1:9)

Vorschrift

4-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile (0.250 g, 0.83 mmol), prepared in Example 4, was dissolved in tetrahydrofuran (2 mL) followed by triethylamine (0.139 mL, 1 mmol) and cyanogen bromide (0.21 g, 2 mmol). The mixture was stirred overnight, filtered and the tetrahydrofuran was removed in vacuo. Purification by normal phase HPLC on a phenomenex cyano column eluting with hexane/1,2-dimethoxyethane (9:1 to 1:9) gave the title compound (0.020 g, 7%). HRMS: calcd for C16H13N5OS+H+, 324.09136; found (ESI, [M+H]+), 324.0919; HPLC purity 100% at 210-370 nm, 9.3 min.; 100% at 246 nm, 9.3 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min, hold 4 min.

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