Reaktion #4214

ord-b1182f573e4048b888b6653ec0ae28f6

Reaktionsgleichung

CC(C)(C)OC(=O)NN1CCNC1=O
N-(2-Oxo-1-imidazolidinyl)carbamic acid, 1,1-dimethylethyl ester
c1ccncc1
pyridine
O=C(Br)CBr
bromoacetyl bromide
CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O
title compound
CC(C)(C)OC(=O)NN1CCN(C(=O)CBr)C1=O
N-[3-(Bromoacetyl)-2-oxo-1-imidazolidinyl]-carbamic acid, 1,1-dimethylethyl ester

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solution was evaporated in vacuo
  2. 2
    Sonstigeto give a yellow oil
  3. 3
    SonstigeThe oil was chromatographed on silica gel (~300 g)
  4. 4
    Wascheneluting with 10% ethyl acetate/dichloromethane
  5. 5
    Sonstigeevaporated in vacuo

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04723002uspto-grants-1988_02