Hydrochloric Acid → 4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline

HRID 1430019Notes

Reaction equation

HRID 1430019 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[N:20]([CH3:21])[C:19]4[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=4[N:17]=3)=[CH:11][CH:10]=2)C=CC=CC=1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:21][N:20]1[C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[N:17]=[C:16]1[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH2:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58577298N-(diphenylmethylidene)-4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline

Product 1

HCID 215636774-[(1-methyl-1H-benzimidazol-2-yl)oxy]anilineYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of N-(diphenylmethylidene)-4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline (810 mg) in THF (10 mL) was added 1 N HCl aq (10 mL) at room temperature, and the mixture was stirred at room temperature for 1 h. The mixture was neutralized with sat. NaHCO3 aq. and extracted with AcOEt. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 5%-100% AcOEt in hexane) to give 4-[(1-methyl-1H-benzimidazol-2-yl)oxy]aniline (440 mg) as colorless crystals.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, eluted with 5%-100% AcOEt in hexane)

Sources & evidence

ORD record
ord-e051715e1c1042e0a510f88fb3fe4a06
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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