Triphenylmethane → 3H-benzoimidazole-5-carboxylic acid N-tert-butyl-N'-(2-ethyl-3-methoxy-benzoyl)-hydrazide

HRID 39639

Reaction equation

HRID 39639 reaction equation
[C:1]([N:5]([C:19]([C:21]1[CH:48]=[CH:47][C:24]2[N:25]=[CH:26][N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:23]=2[CH:22]=1)=[O:20])[NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[K+].O>CO.[Pd]>[C:1]([N:5]([C:19]([C:21]1[CH:48]=[CH:47][C:24]2[N:25]=[CH:26][NH:27][C:23]=2[CH:22]=1)=[O:20])[NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][CH3:17])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10614TriphenylmethaneHCID 23719240Potassium hydroxide monohydrateHCID 598386093-trityl-3H-benzoimidazole-5-carboxylic acid N-tert-butyl-N'-(2-ethyl-3-methoxy-benzoyl)-hydrazide

Product 1

HCID 598386293H-benzoimidazole-5-carboxylic acid N-tert-butyl-N'-(2-ethyl-3-methoxy-benzoyl)-hydrazide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

About 120 mg of 3-trityl-3H-benzoimidazole-5-carboxylic acid N-tert-butyl-N′-(2-ethyl-3-methoxy-benzoyl)-hydrazide were dissolved in 35 mL of CH3OH and added into a hydrogenation bottle, together with 2 drops of glacial acid and 0.20 g Pd/C. Hydrogenation was conducted by shaking the bottle for 6 hours and then remaining under H2 pressure for 16 hours. The Pd/C was removed by filtration and the methanol removed by an evaporator. The residue was stirred with CH2Cl2 and the CH2Cl2 was decanted. Evaporation of the CH2Cl2 yielded a solid product identified by NMR, as triphenylmethane. The residue was stirred with dilute KOH/H2O and extracted with ethyl acetate. The ethyl acetate was dried and concentrated on a rotary evaporator to yield the product 3H-benzoimidazole-5-carboxylic acid N-tert-butyl-N′-(2-ethyl-3-methoxy-benzoyl)-hydrazide. NMR analysis of the product indicated the absorbances for the methoxy and t-Butyl groups occurred at 3.69 and 1.61 vs. 3.77 and 1.59 for the starting material.

Workup

  1. customfor 16 hours
  2. customThe Pd/C was removed by filtration
  3. customthe methanol removed by an evaporator
  4. stirringThe residue was stirred with CH2Cl2
  5. customthe CH2Cl2 was decanted
  6. customEvaporation of the CH2Cl2
  7. customyielded a solid product
  8. extractionextracted with ethyl acetate
  9. dry with materialThe ethyl acetate was dried
  10. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-4cb1656fea52462ab091957e808470a9
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Linked notes

Loading…