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

HRID 4118Notes

Reaction equation

[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1.[Br:21][CH2:22][C:23](Br)=[O:24]>ClCCl>[Br:21][CH2:22][C:23]([N:6]1[CH2:5][CH2:4][N:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[C:2]1=[O:1])=[O:24]

Participants

Conditions

Temperature: 0 °C

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.

Workup

customThe solution was evaporated in vacuo
customto give a yellow oil
customThe oil was chromatographed on silica gel (~300 g)
washeluting with 10% ethyl acetate/dichloromethane
customevaporated in vacuo

Sources & evidence

ORD record: ord-b1182f573e4048b888b6653ec0ae28f6
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04723002

Reaction notes

Loading…