Reaction #81011

Reaction equation

t-butylcarbazate

4-(chloromethyl)-2-isopropylthiazole hydrochloride

→

desired compound

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

Solvents

isopropyl alcohol

isopropyl alcohol

Conditions

Workup

1. 1
   TemperatureThe resulting solution was heated
2. 2
   Temperatureat reflux for 16 h
3. 3
   Temperatureto cool
4. 4
   Concentrationconcentrated in vacuo
5. 5
   workup.ADDITIONThe residue was diluted with 1N HCl
6. 6
   Washwashed with three portions of ethyl acetate
7. 7
   Extractionextracted with three portion of ethyl acetate
8. 8
   DryingThe combined organic layers were dried over MgSO4
9. 9
   Concentrationconcentrated in vacuo
10. 10
    OtherPurification of the residue by silica gel chromatography

Procedure

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.

Source