Cyanogen Bromide → HCID 178419688, compound

HRID 2203407Notes

Reaction equation

HRID 2203407 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[N:10]#[C:11]Br>C(O)C.C(O)(=O)C>[BrH:1].[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:11]([NH2:10])=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 10476Cyanogen BromideHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 178419688HCID 178419688, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-1,2-diaminobenzene (3.0 g, 16 mmol) in a mixture of ethanol (90 mL) and acetic acid (90 mL) was added cyanogen bromide (2.56 g, 24.0 mmol) and the reaction mixture was stirred at ambient temperature for 16 h. The mixture was concentrated in vacuo and the residue was triturated in ethyl acetate (200 mL) to afford 5-bromo-1H-benzo[d]imidazol-2-amine hydrobromide as a brown solid in 85% yield (3.98 g): 1H NMR (300 MHz, DMSO-d6) δ12.49 (br s, 2H), 8.61 (s, 2H), 7.50 (s, 1H), 7.38-7.23 (m, 2H); MS (ES+) m/z 211.9 (M+1), 213.9 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated in ethyl acetate (200 mL)

Sources & evidence

ORD record
ord-c3c3b2027b764a5eb9fa3185199e2364
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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