Nitroethane → 1-Hydroxy-2-methyl-3-oxidobenzimidazol-3-ium

HRID 359555

Reaction equation

HRID 359555 reaction equation
[N+:1]1([O-:10])[O:5][N:4]=[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=12.[N+]([CH2:14][CH3:15])([O-])=O.C(NCC)C>O1CCCC1>[CH3:14][C:15]1[N:4]([OH:5])[C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[N+:1]=1[O-:10]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8021DiethylamineHCID 68075Benzofuroxan

Product 1

HCID 14762771-Hydroxy-2-methyl-3-oxidobenzimidazol-3-iumYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the typical procedure, 0.1 mole of benzofurazan 1-oxide and 0.12 mole of nitroethane is dissolved at 100 ml. of tetrahydrofuran. To this mixture there is added at room temperature, 0.12 mole of diethylamine over a period of 0.5 hour. An instantaneous exothermic reaction is observed (40° C.) and within one hour, the product crystallizes from the solution. The solution is allowed to stand overnight at room temperature and filtered to yield 9.6 grams of 2-methyl-1-hydroxy-1-H-benzimidazole 3-oxide (Table III, Example H-77). The product can be recrystallized from methanol.

Workup

  1. additionTo this mixture there is added at room temperature
  2. customAn instantaneous exothermic reaction
  3. custom(40° C.)
  4. customthe product crystallizes from the solution
  5. waitto stand overnight at room temperature
  6. filtrationfiltered

Sources & evidence

ORD record
ord-36347b557a35406f9617696326cf29be
Source dataset
uspto-grants-1991_03
Patent number
US05001171

Linked notes

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