Water → 5,6-difluoro-1H-1,3-benzodiazol-2-amine

HRID 415124

Reaction equation

HRID 415124 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].O.[N:12]#[C:13]Br.C(=O)([O-])O.[Na+]>C(#N)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[NH:9][C:13]([NH2:12])=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 106787085,6-difluoro-1H-1,3-benzodiazol-2-amineYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-Difluorobenzene-1,2-diamine (0.651 g, 0.562 mmol, commercially available from Matrix Scientific) in acetonitrile (10 mL) and water (2 ml) at 0° C. was treated with cyanogen bromide (0.063 g, 0.6 mmol). The reaction mixture was allowed to warm to room temperature, and then stirred for 14 hours. The reaction mixture was then treated with saturated aqueous sodium hydrogen carbonate solution (50 ml) and shaken. The resulting solid was filtered off, washed with water and dried under reduced pressure to give 0.39 g of 5,6-difluoro-1H-benzo[d]imidazol-2-amine (yield, 40%). MS (EI): 186 (MH+).

Workup

  1. stirringshaken
  2. filtrationThe resulting solid was filtered off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d0e0bd4bbee149338404daac09d120bf
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Linked notes

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