p-Tolunitrile → 1-(3-Ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazole-4-carboxylic acid

HRID 2356593Notes

Reaction equation

HRID 2356593 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

8

Reactant 5

HCID 7724p-TolunitrileHCID 8028Tetrahydrofuran2×HCID 121203-EthoxyanilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178466607HCID 178466607, compound

Product 1

HCID 593841541-(3-Ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

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

  1. stirringThe resulting mixture was stirred at ambient temperature for 5 hrs
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76ab3ba3a1034b6b91da825298dc2de0
Source dataset
uspto-grants-2010_07
Patent number
US07759352B2

Reaction notes

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