Reaction #4214

Reaction equation

N-(2-Oxo-1-imidazolidinyl)carbamic acid, 1,1-dimethylethyl ester

pyridine

bromoacetyl bromide

→

title compound

N-[3-(Bromoacetyl)-2-oxo-1-imidazolidinyl]-carbamic acid, 1,1-dimethylethyl ester

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe solution was evaporated in vacuo
2. 2
   Otherto give a yellow oil
3. 3
   OtherThe oil was chromatographed on silica gel (~300 g)
4. 4
   Washeluting with 10% ethyl acetate/dichloromethane
5. 5
   Otherevaporated in vacuo

Procedure

N-(2-Oxo-1-imidazolidinyl)carbamic acid, 1,1-dimethylethyl ester (12.0 g, 0.06 mmol) was dissolved in dichloromethane (75 ml) containing pyridine (5.2 g, 0.066 mol). The solution was cooled to 0° C. and treated slowly with bromoacetyl bromide (13.3 g, 0.066 mol). The solution was evaporated in vacuo to give a yellow oil. The oil was chromatographed on silica gel (~300 g) eluting with 10% ethyl acetate/dichloromethane. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white solid, 16.7 g.

Source