p-Tolunitrile → 1-(3-Ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazole-4-carboxylic acid
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[NH:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C([O:32][C:33]1C=C(C=[CH:38][CH:39]=1)N)C.C1(C)C=CC(C#N)=CC=1.[O:49]1CCCC1>[Cl-].[Na+].O.ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:38]=[C:39]([C:33]([OH:32])=[O:49])[N:12]=[C:11]2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
N-(3-Ethoxyphenyl)-4-methylbenzenecarboxamidine To a solution of 2.2 ml (4.4 mmol) of 2.0 M (in tetrahydrofuran) sodium bis(trimethylsilyl)amide in 5.0 mL of tetrahydrofuran at ambient temperature was added 0.52 mL (4.0 mmol) of 3-ethoxyaniline and the resulting solution was stirred for 20 min. To this reaction mixture was slowly added a solution of 0.47 g (4.0 mmol) of p-tolunitrile in 2.0 mL of tetrahydrofuran. The resulting mixture was stirred at ambient temperature for 5 hrs and then poured into brine (25 mL) and dichloromethane (50 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (25 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield the title compound as yellow solid, which was used without further purification. LC/MS 255.2 (M+1).
Workup
- stirringThe resulting mixture was stirred at ambient temperature for 5 hrs
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with dichloromethane (25 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-88d1e5c1a3bb46b680d896bf341f4ee9
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07858629B2
Reaction notes
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