Formic Acid → N-{1-[1-(3-Bromo-phenyl)-1H-benzoimidazol-5-yl]-ethyl}-formamide

HRID 2262744Notes

Reaction equation

HRID 2262744 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17](=O)[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:20]([NH2:22])=[O:21].C(O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([CH:17]([NH:22][CH:20]=[O:21])[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 284Formic AcidHCID 713FormamideHCID 540303071-(1-(3-bromophenyl)-1H-benzo[d]imidazol-5-yl)ethanone

Product 1

HCID 57572242N-{1-[1-(3-Bromo-phenyl)-1H-benzoimidazol-5-yl]-ethyl}-formamideYield 60%

Conditions

Temperature
190 °C

Procedure

A mixture of 1-[1-(3-bromo-phenyl)-1H-benzoimidazol-5-yl]-ethanone (7.5 g, 23.8 mmol), formamide (9.5 ml, 23.8 mmol) and formic acid (22.4 ml, 595 mmol) was stirred at 190° C. for 7 hours. The cooled mixture was decanted. The residue was rendered alkaline by addition of saturated, aqueous sodium carbonate and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate and concentrated in vacuo. The concentrate was eluted through silica gel with a mixture of dichloromethane, methanol and aqueous ammonia (9:1:0.1 v/v/v) to afford the desired product (60%).

Workup

  1. customThe cooled mixture was decanted
  2. additionby addition of saturated, aqueous sodium carbonate
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. washThe concentrate was eluted through silica gel with a mixture of dichloromethane, methanol and aqueous ammonia (9:1:0.1 v/v/v)

Sources & evidence

ORD record
ord-f780767cce164e6fad9c10d0134034ce
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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