1-methyl-1H-1,3-benzodiazol-5-amine → HCID 12968444, compound

HRID 2186069Notes

Reaction equation

HRID 2186069 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:5]=2[N:4]=[CH:3]1>C(O)C(C)C>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:3]3[NH:4][CH2:5][CH2:6][N:2]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

3

Reactant 1

HCID 3154991-methyl-1H-1,3-benzodiazol-5-amine

Product 1

HCID 12968444HCID 12968444, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of 1-methyl-5-aminobenzimidazole (0.15 g, 1.1 mmol) and ISA (0.30 g, 2.2 mmol) in 3 ml of isobutanol was stirred at reflux for 12 h. The reaction mixture was concentrated in vacuo, yielding an oily residue which was purified on silica gel column chromatography (NH3 sat'd 20% isopropanol/EtOAc) to yield 0.12 g (0.56 mmol, 51%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from isopropanol to afford 0.11 g (30%) of the product as a white crystal: mp 210-211° C.; Anal. Calc. for C11H13N5.1.0C4H4O4-0.3H2O requires C, 35.36; H. 5.28; N,20.74. Found: C, 53.67; H, 5.13; N, 20.70.

Workup

  1. temperatureat reflux for 12 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customyielding an oily residue which
  4. customwas purified on silica gel column chromatography (NH3 sat'd 20% isopropanol/EtOAc)

Sources & evidence

ORD record
ord-2c50c4f1fdc541ca9572ff12b180d683
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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