Sodium Hydroxide → 1-Methyl-5-nitro-1H-benzimidazol-2-amine

HRID 1391547Notes

Reaction equation

HRID 1391547 reaction equation
[CH3:1][NH:2][C:3]1[C:4]([NH2:12])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1.[N-:13]=[C:14]=S.[Br-].[OH-].[Na+]>CO>[CH3:1][N:2]1[C:3]2[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=2[N:12]=[C:14]1[NH2:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 34200251-N-methyl-4-nitrobenzene-1,2-diamineHCID 178419725HCID 178419725, compound

Product 1

HCID 450786361-Methyl-5-nitro-1H-benzimidazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of N1-Methyl-4-nitro-benzene-1,2-diamine (5 g, 30 mmol) in MeOH was added bromide isothiocyanate (4.4 g, 42 mmol) and the mixture was stirred at rt. After 16 h. 6N NaOH solution was added to the reaction mixture until Ph˜10 and MeOH was then removed in vacuo. H2O was added and the solid was filtered and dried to give the title compound as an off white solid (5.2 g, 90%). MS (ESI) m/z=193 [M+H]+.

Workup

  1. customwas then removed in vacuo
  2. additionH2O was added
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-b2b71a75ab654a4c9e9d2aba2c7a4fee
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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