Nitromethane → 1H-benzimidazol-1-ol 3-oxide

HRID 1607719

Reaction equation

HRID 1607719 reaction equation
[N+]([CH3:4])([O-])=O.[CH:5]1[CH:13]=[CH:12][C:11]2[C:7](=[N:8][O:9][N+:10]=2[O-:14])[CH:6]=1.CC1N=CN=C(C)C=1>O1CCCC1>[OH:9][N:8]1[C:7]2[CH:6]=[CH:5][CH:13]=[CH:12][C:11]=2[N+:10]([O-:14])=[CH:4]1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 152574,6-DimethylpyrimidineHCID 68075Benzofuroxan

Product 1

HCID 123493471H-benzimidazol-1-ol 3-oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture containing nitromethane (7.4 g., 0.12 moles), benzofuroxan 13.6 g., 0.10 moles) and tetrahydrofuran (50 ml.) is slowly added dimethylpyrimidine (11.3 g.) dropwise. The heat of reaction causes the reaction temperature to rise sharply; therefore, an ice-bath is used to maintain a steady rate of reflux. Upon completion of addition, the resulting mixture is allowed to cool to room temperature whereupon the solid product which precipitates is filtered, washed with water, dried and recrystallized from a MeOH/NaOCH3 mixture which is subsequently acidified. The crystalline product has an M.P. 213° C. dec.

Workup

  1. temperatureThe heat of reaction
  2. customtherefore, an ice-bath is used
  3. temperatureto maintain a steady rate
  4. temperatureof reflux
  5. additionUpon completion of addition
  6. customprecipitates
  7. filtrationis filtered
  8. washwashed with water
  9. customdried
  10. customrecrystallized from a MeOH/NaOCH3 mixture which

Sources & evidence

ORD record
ord-7e53e56e1e234f45b968485bf6b00ec8
Source dataset
uspto-grants-1989_09
Patent number
US04866175

Linked notes

Loading…