2-(1H-Benzimidazol-2-yl)aniline → HCID 12668461, compound

HRID 2265051Notes

Reaction equation

HRID 2265051 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].[CH2:17]([Li])CCC>C1COCC1.CCOCC>[CH3:17][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16]

Participants

5

Reactant 2

HCID 798692-(1H-Benzimidazol-2-yl)anilineHCID 178418339Butyllithium

Product 1

HCID 12668461HCID 12668461, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(1H-benzo[d]imidazol-2-yl)benzenamine (525 mg, 2.5 mmol) in 5 mL dry THF was cooled to −78 degrees before 1 mL n-Bu-Li (2.5 mmol, 2.5 N in hexanes) was added via a syringe. The reaction was stirred at −78 degrees for 20 min and Mel (360 mg, 2.6 mmol) was added. The reaction was warmed to r.t. gradually and kept at room temperature for another hour. The reaction crude was diluted with 25 mL ether and the resulted suspension was filtered off the solid. The crude product was isolated after the solvent was removed from the collected filtrate to product 510 mg of 2-(1-methyl-1H-benzo[d]imidazol-2-yl)benzenamine in greater than 95% purity (MS, M++H=224.1).

Workup

  1. additionwas added via a syringe
  2. additionMel (360 mg, 2.6 mmol) was added
  3. waitkept at room temperature for another hour
  4. customThe reaction crude
  5. filtrationthe resulted suspension was filtered off the solid

Sources & evidence

ORD record
ord-5e375d7ca998408e9727a9edfcf7c573
Source dataset
uspto-grants-2010_12
Patent number
US07855289B2

Reaction notes

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