N-bromobutanimide → HCID 59771167, compound

HRID 1190166Notes

Reaction equation

HRID 1190166 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[CH:9][N:10]=1)=[O:5])[CH3:2].C1C(=O)N([Br:26])C(=O)C1>CC#N>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[CH:8]=[C:9]([Br:26])[N:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59771301HCID 59771301, compound

Product 1

HCID 59771167HCID 59771167, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid ethyl ester (0.20 g, 0.74 mmol)(as prepared in the previous step) in 2 mL of CH3CN was added NBS (0.13 g, 0.74 mmol) and the mixture heated to 60° C. for 2 h. The mixture was concentrated and the title compound purified by elution from a 20-g SPE column with 20% EtOAc/hexanes to give 0.1 g (39%) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H21BrN2O3Si, 349.0 (M+H). found 348.7.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe title compound purified by elution from a 20-g SPE column with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-7dcf1dca2e734ae2b1d5d683de72083b
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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