Water → HCID 22285481, compound

HRID 1062435Notes

Reaction equation

HRID 1062435 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[CH3:25])=[CH:4][CH:3]=1.[Br:26]N1C(=O)CCC1=O.O>CCO>[Br:26][C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[CH3:25])=[N:10][C:11]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 22285508HCID 22285508, compound

Product 1

HCID 22285481HCID 22285481, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-(4-chlorophenyl)-2-(2,4-dimethylphenyl)-1H-imidazole-4-carboxylate (1.23 g, 3.47 mmol) was dissolved in EtOH (15 mL) and treated with N-bromosuccinimide (1.25 g, 7.02 mmol). The solution was stirred at rt for 3 h. Water was added. Extraction with dichloromethane, which was then washed with NaCl solution, gave an orange solid (1.94 g). Purification by chromatography over silica gel (20% EtOAc in hexane) afforded a light tan solid (1.028 g, 68%): 1H NMR (300 MHz, CDCl3) δ 7.35 (d, 2H), 7.03 (d, 2H), 7.00 (m, 1H), 6.86 (m, 2H), 4.44 (q, 2H), 2.26 (s, 3H), 2.10 (s, 3H), 1.43 (t, 3H); LC-MS m/z 433.1 (MH+), retention time 3.84 min (method 1).

Workup

  1. extractionExtraction with dichloromethane, which
  2. washwas then washed with NaCl solution

Sources & evidence

ORD record
ord-73ce41c22bc445f7be960f84d5f5d51a
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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