Chloroform → 1H-Benzimidazol-6-amine,1,2-dimethyl-(9CI)

HRID 230851Notes

Reaction equation

HRID 230851 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][N:7]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH3:19].C(Cl)(Cl)Cl.[OH-].[Na+]>Cl>[CH3:6][N:7]1[C:11]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH3:19]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 13327865HCID 13327865, compound

Product 1

HCID 122280631H-Benzimidazol-6-amine,1,2-dimethyl-(9CI)

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of tin (II) chloride dihydrate (4.7 g) in concentrated hydrochloric acid (15 ml) was added 1,2-dimethyl-6-nitro-1H-benzimidazole (1 g) (J. Chem. Soc.,1931, 1143-1153), and the mixture was stirred at room temperature for 6 h. The mixture was poured onto ice and chloroform, and basified to pH 10 by the addition of 10M sodium hydroxide solution. The mixture was extracted several times with chloroform and the combined organic extracts dried and concentrated in vacuo to give a brown solid. This was crystallised from ethanol to give the title compound.

Workup

  1. extractionThe mixture was extracted several times with chloroform
  2. customthe combined organic extracts dried
  3. concentrationconcentrated in vacuo
  4. customto give a brown solid
  5. customThis was crystallised from ethanol

Sources & evidence

ORD record
ord-15e3655b520144ca863276a4bcec9132
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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