Sodium Hydroxide → HCID 178436222, compound

HRID 991595Notes

Reaction equation

HRID 991595 reaction equation
[NH2:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:12]([C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:15]=1[CH:16]=O)[CH3:13].[BH3-]C#N.[Na+].[OH-].[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH2:22]([C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([CH2:12][CH3:13])[C:15]=1[CH2:16][NH:1][C:2]1[C:10]2[NH:9][C:8]([CH3:11])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH3:23]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131847782,6-DiethylbenzaldehydeHCID 178432166HCID 178432166, compound

Product 1

HCID 178436222HCID 178436222, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

4-Amino-2-methylbenzimidazole (0.79 g, 5.4 mmol) and 2,6-diethylbenzaldehyde (1.1 g, 6.6 mmol) were dissolved in methanol (30 ml). ZnCl2 (0.9 g, 6.6 mmol) and subsequently NaBH3CN (0.42 g, 6.6 mmol) in small portions were added and the mixture was refluxed under argon for 3 hours and was stirred at room temperature for 16 h. The mixture was poured over an aqueous 1M NaOH solution (50 ml). The resultant yellow suspension was extracted with DCM and the organic solution was washed with brine, dried over Na2SO4 and then evaporated under reduced pressure. The oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile to give 0.65 g (41%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed under argon for 3 hours
  2. extractionThe resultant yellow suspension was extracted with DCM
  3. washthe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe oily residue (1.8 g) was purified by crystallization from a mixture of ethyl acetate and acetonitrile

Sources & evidence

ORD record
ord-4455fb3659784a0da15e42715ebbaf7f
Source dataset
uspto-grants-2002_10
Patent number
US06465505B1

Reaction notes

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