1,1'-Carbonyldiimidazole → 5-Bromo-1,3-dihydro-2H-benzimidazol-2-one

HRID 1051469Notes

Reaction equation

HRID 1051469 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.C1N=CN([C:15](N2C=NC=C2)=[O:16])C=1>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:15](=[O:16])[NH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 122280605-Bromo-1,3-dihydro-2H-benzimidazol-2-oneYield 128%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of 4-bromobenzene-1,2-diamine (200 mg, 1.1 mmol), CDI (174 mg, 1.1 mmol) in dioxane was reacted at 50° C. for 16 hours. The mixture was concentrated and the residue was dissolved in DCM and extracted with water with the combined organic phases dried by Na2SO4 and concentrated to give 300 mg of crude product which was used without further purification. LCMS (m/z): 213.1/214.1 [M+H]+/[M+2H]+

Workup

  1. customwas reacted at 50° C. for 16 hours
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue was dissolved in DCM
  4. extractionextracted with water with the combined organic phases
  5. dry with materialdried by Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-70bffae8f78a4835a31b4a8750769e7a
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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