HCID 178507337, compound → HCID 178419417, compound

HRID 2299117Notes

Reaction equation

HRID 2299117 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:11]>C(O)C(C)C>[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11][C:8]1[NH:9][CH2:10][CH2:6][N:7]=1

Participants

3

Reactant 1

HCID 178507337HCID 178507337, compound

Product 1

HCID 178419417HCID 178419417, compoundYield 171.1%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of 4-bromo-5-aminobenzimidazole (0.22 g, 0.97 mmol) and ISA (0.34 g, 2.5 mmol) in 5 ml of isobutanol was stirred at reflux for 12 h. Reaction mixture was concentrated in vacuo and subjected to silica gel column chromatography (NH3 saturated 20% MeOH/EtOAc) to yield 0.23 g (0.83 mmol, 84%) of the product. The product obtained was converted to the fumarate salt and recrystallized from MeOH to afford 0.12 g (30%) of the product as a white solid: mp 199-202° C.; Anal. Calc. for CO10H10N5Br.1.0C4H4.0.7H2O requires C, 41.13; H, 3.80; N, 17.13. Found: C, 41.60; H, 3.81; N, 16.97.

Workup

  1. temperatureat reflux for 12 h
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-972c42f9c2b1456fb213582faeeac9d2
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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