Reaktion #81011

Reaktionsgleichung

t-butylcarbazate

4-(chloromethyl)-2-isopropylthiazole hydrochloride

→

desired compound

2-Isopropyl-4-((N-(tert-butyloxycarbonylamino)amino)methyl)thiazole

Lösungsmittel

isopropyl alcohol

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting solution was heated
2. 2
   Temperaturat reflux for 16 h
3. 3
   Temperaturto cool
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.ADDITIONThe residue was diluted with 1N HCl
6. 6
   Waschenwashed with three portions of ethyl acetate
7. 7
   Extraktionextracted with three portion of ethyl acetate
8. 8
   TrocknenThe combined organic layers were dried over MgSO4
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigePurification of the residue by silica gel chromatography

Vorschrift

A solution of 7.5 g (57 mmol) to t-butylcarbazate in 200 ml of isopropyl alcohol was treated with a solution of 1.0 g (57 mmol) of 4-(chloromethyl)-2-isopropylthiazole hydrochloride in 10 ml of isopropyl alcohol. The resulting solution was heated at reflux for 16 h, allowed to cool, and concentrated in vacuo. The residue was diluted with 1N HCl, washed with three portions of ethyl acetate, basified to pH 12 with aqueous NaOH, and extracted with three portion of ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification of the residue by silica gel chromatography using 20% ethyl acetate in hexane provided 0.32 g (21%) of the desired compound (Rf 0.4, 5% methanol in chloroform). 1H NMR (CDCl3) δ1.40 (d, J=7 Hz, 6H), 1.47 (s, 9H), 2.53 (br, 1H), 3.33 (heptet, J=7 Hz, 1H), 4.11 (s, 2H), 6.22 (br, 1H), 7.01 (s, 1H). Mass spectrum: (M+H)+ =272.

Quelle