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

HRID 66955

Reaction equation

HRID 66955 reaction equation
[N+]([CH2:4][CH3:5])([O-])=O.[CH:6]1[CH:14]=[CH:13][C:12]2[C:8](=[N:9][O:10][N+:11]=2[O-:15])[CH:7]=1.C(NCC)C>O1CCCC1>[OH:10][N:9]1[C:8]2[CH:7]=[CH:6][CH:14]=[CH:13][C:12]=2[N+:11]([O-:15])=[C:4]1[CH3:5]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8021DiethylamineHCID 68075Benzofuroxan

Product 1

HCID 14762771-Hydroxy-2-methyl-3-oxidobenzimidazol-3-ium

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture containing nitroethane (9.0 g., 0.12 moles), benzofuroxan (13.6 g., 0.10 moles) and tetrahydrofuran (50 ml.) is added dropwise diethylamine (8.7 g., 0.12 moles). The reaction temperature rises almost to reflux upon addition. Upon completion, the mixture is allowed to cool and to stand overnight.

Workup

  1. temperatureto reflux upon addition
  2. temperatureto cool

Sources & evidence

ORD record
ord-fb39d91871ac4d79ab4bfb26ee4baec4
Source dataset
uspto-grants-1982_08
Patent number
US04343942

Linked notes

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