Imidazole → 3-(N-imidazolyl)-2-nitrobenzofuran

HRID 614360Notes

Reaction equation

HRID 614360 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CN(C)C=O.[H-].[Na+].Br[C:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][C:15]=1[N+:23]([O-:25])=[O:24]>O>[N:1]1([C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[N+:23]([O-:25])=[O:24])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 135098423-Bromo-2-nitro-1-benzofuran

Product 1

HCID 213293813-(N-imidazolyl)-2-nitrobenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 0.1 g. (12 mmole) of imidazole in 20 ml. of N,N-dimethylformamide is added 0.5 g. (12 mmole) of 57.6 percent suspension of sodium hydride in mineral oil. After cooling to 20° C., 2.4 g. (10 mmole) of 3-bromo-2-nitrobenzofuran in 20 ml. of N,N-dimethylformamide is added. After stirring 45 minutes, the mixture is heated on a steam bath for 15 minutes, then 50 ml. of water are added. Cooling and filtration provide yellow needles of 3-(N-imidazolyl)-2-nitrobenzofuran, m.p. 147°-149° C.

Workup

  1. temperaturethe mixture is heated on a steam bath for 15 minutes
  2. temperatureCooling
  3. filtrationfiltration

Sources & evidence

ORD record
ord-037d7bfbdbab438c8fdaaffe6a5cef9a
Source dataset
uspto-grants-1979_03
Patent number
US04144347

Reaction notes

Loading…