2-Chlorobenzimidazole → 2-Aminobenzimidazole

HRID 1243672Notes

Reaction equation

HRID 1243672 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1CN.Cl[C:11]1[NH:12]C2C=CC=CC=2[N:15]=1>C(Cl)Cl>[N:1]1[C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[NH:12][C:11]=1[NH2:15]

Participants

4

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 1780962-(Aminomethyl)aniline

Product 1

HCID 136242-AminobenzimidazoleYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-aminobenzylamine (500 mg, 4.1 mmol) and 2-chlorobenzoimidazole (305 mg, 2.0 mmol) was heated at 110° C. for 18 h. The resulting solid was dissolved in CH2Cl2 (30 mL) and washed with H2O (30 mL). The organic layer was separated, dried over Na2SO4, and concentrated to provide crude benzimidazole-amine (200 mg) which was treated with CDI (500 mg, 3.0 mmol) in anhydrous DMF (15 mL). After stirring at RT for 18 h, the reaction mixture was concentrated and the viscous residue was triturated with CH2Cl2. The precipitates were filtered and recrystallized from DMSO (3 mL) and CH2Cl2 (0.5 mL) to afford the title compound as an off-white solid. MS m/z: 265 (M+H+). Anal. Calc'd for C15H12N4O: C, 68.17; H, 4.58; N, 21.20; O, 6.05; Found C, 68.35; H, 4.71; N, 21.27; O, 6.04.

Workup

  1. washwashed with H2O (30 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3808a588137347128c1c5c3639417e2e
Source dataset
uspto-grants-2006_10
Patent number
US07119111B2

Reaction notes

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