Benzene → HCID 86703998, compound

HRID 1773916Notes

Reaction equation

HRID 1773916 reaction equation
[CH3:1]O[Na].CN1[C:9](=O)[CH2:8][CH2:7][CH2:6]1.[C:11]1([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:22]1[CH:27]=[CH:26]C=[CH:24][CH:23]=1>CO>[CH3:6][C:7]([N:20]1[CH:21]=[C:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:18]=[CH:19]1)([CH3:1])[CH2:8][C:9]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 13387N-methyl-2-pyrrolidoneHCID 178418582HCID 178418582, compoundHCID 178418822HCID 178418822, compound

Product 1

HCID 86703998HCID 86703998, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
170 °C

Procedure

To a freshly prepared MeONa solution in MeOH (10 mL MeOH and 0.23 g Na metal) are added NMP (10 mL), 4-phenyl-1H-imidazole (1.44 g, 10 mmoles) and 2-chloro-2-methylpropyl)-benzene (1.69 g, 10 mmoles). The reaction mixture is heated at 170° C. (MeOH distilled and evacuated) for 24 hours. NMP is removed under reduced pressure. AcOEt is added and the organic phase is washed with water, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH) as eluent with a gradient from (100:0) to (98:2) to give 1-(1,1-dimethyl-2-phenylethyl)-4-phenyl-1H-imidazole.

Workup

  1. distillation(MeOH distilled and evacuated) for 24 hours
  2. customNMP is removed under reduced pressure
  3. additionAcOEt is added
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. customThe residue is pre-purified by silica gel chromatography

Sources & evidence

ORD record
ord-1b056b2bd4f64baebcd08138c4ba2a8b
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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