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

HRID 2112822Notes

Reaction equation

HRID 2112822 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Br:13][C:14]1[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=1>CN(C=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]2[NH:20][C:1](=[O:2])[NH:21][C:16]=2[CH:15]=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-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4.29 g (26.46 mmol) of carbonyldiimidazole (CDI) is added to a solution of 4.5 g (24.05 mmol) of 4-bromobenzene-1,2-diamine in 95 mL of DMF and the reaction mixture is stirred for 5 hours at 80° C. Then the reaction mixture is poured onto water and the precipitate formed is filtered off. The precipitate is washed three times with water and dried in the circulating air dryer at 60° C. Yield: 4.6 g (90% of theoretical); C7H5BrN2O (M=213.03); calc.: molpeak (M+H)+: 213/215; found: molpeak(M+H)+: 213/215; Rf value: 0.5 (silica gel, DCM/MeOH 10:1).

Workup

  1. additionThen the reaction mixture is poured onto water
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washThe precipitate is washed three times with water
  5. customdried in the circulating air dryer at 60° C

Sources & evidence

ORD record
ord-57cae01db86643fc80de27d9654d7aec
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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