Water → HCID 58709968, compound

HRID 2375906Notes

Reaction equation

HRID 2375906 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br.Br[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].[H-].[Na+].O>CN(C=O)C>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][N:14]1[CH:13]=[CH:12][N:11]=[C:10]1[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8210012-(3-nitrophenyl)-1H-imidazoleHCID 457913472-Bromoethyldimethylammonium bromide

Product 1

HCID 58709968HCID 58709968, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At rt and under N2, to a solution of 2-(3-nitrophenyl)-1H-imidazole (0.189 g, 1.00 mmol) and (2-bromoethyl)dimethylamine hydrobromide (0.280 g, 1.20 mmol) in anhydrous DMF (5 mL) was added NaH (60% in mineral oil, 160 mg, 4.0 mmol) in two portions with caution. The mixture was stirred at rt for 15 h. Water (0.3 mL) was added cautiously to quench the reaction. Solvent was removed in vacuo, and the residue was purified by silica gel chromatography (5% MeOH in dichloromethane) to afford the title compound. 1H-NMR (CDCl3, 400 MHz): δ=2.24 (s, 6H), 2.69 (t, J=7.2 Hz, 2H), 4.13 (d, J=6.8 Hz, 2H), 7.17 (d, J=1.2 Hz, 1H), 7.19 (d, J=1.2 Hz, 1H), 7.65 (t, J=8.0 Hz, 1H), 8.04(dt, J=0.8, 8.0 Hz, 1H), 8.28 (dq, J=1.2, 8.4 Hz, 1H), 8.56 (t, J=1.6 Hz, 1H). MS (ES+): m/z 261.17 [MH+]. HPLC: tR=0.46 min (ZQ2000, polar—5 min).

Workup

  1. customto quench
  2. customthe reaction
  3. customSolvent was removed in vacuo
  4. customthe residue was purified by silica gel chromatography (5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-e1d40f23db9648e29b344718513fd941
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…