Cyanogen Bromide → 1155599-04-4

HRID 885451Notes

Reaction equation

HRID 885451 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:11])=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1)[CH3:2].[N:12]#[C:13]Br.[NH4+].[OH-]>CO.O>[CH2:1]([N:3]1[C:4]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=2[N:11]=[C:13]1[NH2:12])[CH3:2]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 14923Ammonium HydroxideHCID 21286303N~1~-Ethyl-4-fluorobenzene-1,2-diamine

Product 1

HCID 436615721155599-04-4

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N1-ethyl-4-fluoro-benzene-1,2-diamine (1.54 g, 10.0 mmol) in MeOH (20 mL) and H2O (20 mL) was added cyanogen bromide (2.1 mL, 10.5 mmol, 5.0 M in acetonitrile). The resulting mixture was stirred at room temperature overnight. The resulting mixture was then adjusted to pH>9 with concentrated NH4OH and the resulting solid was collected by filtration, washed with H2O and hexanes to yield 1-ethyl-5-fluoro-1H-benzimidazol-2-ylamine MS 180 (M+1)+.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with H2O and hexanes

Sources & evidence

ORD record
ord-7eb9fcc163f946ba80e738d92200f61d
Source dataset
uspto-grants-2012_08
Patent number
US08242157B2

Reaction notes

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