HCID 178507224, compound → HCID 10468857, compound

HRID 429578Notes

Reaction equation

HRID 429578 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([NH2:11])[CH:3]=1>C(O)C(C)C>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[CH:5]=[C:4]([NH:11][C:8]2[NH:9][CH2:10][CH2:6][N:7]=2)[CH:3]=1

Participants

3

Reactant 1

HCID 178507224HCID 178507224, compound

Product 1

HCID 10468857HCID 10468857, compoundYield 157.9%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

4-bromo-6-aminobenzimidazole (0.4 g, 1.9 mmol) and ISA (1.2 g, 8.9 mmol) was dissolved in isobutanol and stirred at reflux for 12 h. Column chromatographic separation of the reaction mixture (NH3 sat'd 20% MeOH/EtOAC) provided 0.41 g (1.5 mmol, 78%) of the product. The product obtained was converted to the fumarate salt and recrystallized from isopropanol to afford 0.24 g (32%) of the product as a light brown solid: mp 217-218° C.; Anal. Calc. for C10H10N5Br. 1.0C4H4O4 requires C, 42.44; H, 3.56; N, 17.68. Found: C, 42.28; H, 3.58; N, 17.40.

Workup

  1. temperatureat reflux for 12 h
  2. customColumn chromatographic separation of the reaction mixture (NH3 sat'd 20% MeOH/EtOAC)

Sources & evidence

ORD record
ord-8885c92ca5694a058aa1d64235e91dc0
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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