Sodium Hydroxide → HCID 178484274, compound

HRID 1886048Notes

Reaction equation

HRID 1886048 reaction equation
[CH3:1][N:2]([CH2:11][CH2:12][N:13]([CH3:26])[C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:16]=2[N:15]=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.O.Cl[Sn]Cl.[OH-].[Na+]>CCO>[CH3:1][N:2]([CH2:11][CH2:12][N:13]([CH3:26])[C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:16]=2[N:15]=1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 178484275HCID 178484275, compound

Product 1

HCID 178484274HCID 178484274, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-methyl-N-[2-[methyl(5-nitro-1H-benzimidazol-2-yl)amino]ethyl]benzamide (1.30 g, 3.68 mmol) and SnCl2.2H2O (4.15 g, 18.39 mmol) in EtOH (15 mL) was heated under reflux for 1 hour. The mixture was cooled and made basic (pH8) with 2.5N NaOH. The precipitate was removed by filtration and the filtrate was concentrated. The residue was stirred with EtOAc (150 mL) overnight, dried (MgSO4), and concentrated to give 1.12 g (94%) of a green foam.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was cooled
  4. customThe precipitate was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b170a3f7e7954ead93f3de87c93d82f3
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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