Reaction #699503

Reaction equation

N-(2-Aminoethyl)-(2-nitroimidazol-1-yl)acetamide

2-oxo-1,4-dithiane

→

N-(2-[(2-mercaptoethylthio)acetylamino]ethyl)-(2-nitroimidazol -1-yl)acetamide

Yield 37.5%

Solvents

methanol

acetone

Conditions

Workup

1. 1
   workup.WAITThe mixture was left at room temperature
2. 2
   OtherThe bulk of the solvent was removed
3. 3
   Otherthe resulting material purified by reverse phase h.p.l.c

Procedure

N-(2-Aminoethyl)-(2-nitroimidazol-1-yl)acetamide (40 mg, 0.23 mmol) in methanol (0.5 cm3) was added to 2-oxo-1,4-dithiane (40 mg, 0.27 mmol) in acetone (0.2 cm3) under an atmosphere of dry nitrogen. The mixture was left at room temperature and monitored by n.m.r. spectroscopy until the reaction was complete. The bulk of the solvent was removed, and the resulting material purified by reverse phase h.p.l.c. using aqueous methanol as the eluant. The pure N-(2-[(2-mercaptoethylthio)acetylamino]ethyl)-(2-nitroimidazol -1-yl)acetamide (30 mg) was isolated as a pale yellow solid.

Source