Sodium Hydroxide → HCID 19867702, compound

HRID 1198935Notes

Reaction equation

HRID 1198935 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[CH3:20])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[CH3:20])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19867703HCID 19867703, compound

Product 1

HCID 19867702HCID 19867702, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (45.9 g) was added portionwise to a stirred solution of 1-(3-methyl-4-nitrophenyl)-2-methylbenzimidazole (9.2 g) in absolute ethanol (200 cm3) under nitrogen. After heating under reflux for 1 hour, the cooled mixture was basified to pH 9 with aqueous 2.5M sodium hydroxide and extracted with chloroform (3×200 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give the title compound (8.9 g) which was characterised spectroscopically then used directly in Preparation 12 without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with chloroform (3×200 cm3)
  4. dry with materialdried (MgSO4) organic extracts
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-1e5e7d700dda41bca2023a71b4b8f403
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

Loading…