Imidazole → HCID 22459644, compound

HRID 2185098Notes

Reaction equation

HRID 2185098 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[OH-].[K+].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>CS(C)=O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisole

Product 1

HCID 22459644HCID 22459644, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-chloro-5-nitroanisole (1.0 g, 5.33 mmol), KOH (0.438 g, 7.81 mmol) and imidazole (1.45 g, 21.3 mmol) in DMSO (5 mL) was heated to 80° C. for three hours. The reaction mixture was poured into ice water. The precipitate was collected and washed with water to afford the title compound (0.75 g, 64%). 1H NMR (CDCl3): δ8.84 (1H, s), 8.07 (2H, m), 7.66 (1H, d), 7.55 (1H, s), 7.44 (1H, s), 4.09 (3H, s); LC-MS: m/z 220.07 (M+H)+

Workup

  1. customThe precipitate was collected
  2. washwashed with water

Sources & evidence

ORD record
ord-c34fe711b07d4286a772b66abd0c9df4
Source dataset
uspto-grants-2002_06
Patent number
US06399773B1

Reaction notes

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