2-Aminobenzimidazole → HCID 58362394, compound

HRID 2361486Notes

Reaction equation

HRID 2361486 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:17][CH:16]=1)=[O:14]>CO>[NH2:1][C:2]1[N:6]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[CH:17][CH:16]=2)=[O:14])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 136242-AminobenzimidazoleHCID 27950302-bromo-1-[4-(diethylamino)phenyl]ethanone

Product 1

HCID 58362394HCID 58362394, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-aminobenzimidazole (197 mg, 1.5 mmol) and 2-Bromo-4′-(diethylamino)acetophenone (402 mg, 1.5 mmol) in MeOH (7 mL) was stirred at r.t. for 18 hours. The volatiles were removed in vacuo and NaHCO3 (sat. aq., 30 mL) was added. The aqueous mixture was extracted with EtOAc (3×30 mL). The combined EtOAc extracts were dried with MgSO4 and concentrated in vacuo. The residue was purified on silica gel eluting with a gradient up to 5:95 (MeOH:DCM) to isolate 2-(2-amino-1H-benzo[d]imidazol-1-yl)-1-(4-(diethylamino)phenyl)ethanone (176 mg, 36%) as a beige solid.

Workup

  1. customThe volatiles were removed in vacuo and NaHCO3 (sat. aq., 30 mL)
  2. additionwas added
  3. extractionThe aqueous mixture was extracted with EtOAc (3×30 mL)
  4. dry with materialThe combined EtOAc extracts were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel eluting with a gradient up to 5:95 (MeOH:DCM)

Sources & evidence

ORD record
ord-83d5ecc02bec476b984d748ecec25da2
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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