Acetic Acid → HCID 343062, compound

HRID 636753Notes

Reaction equation

HRID 636753 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=[O:18])C.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+]>ClCCCl>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[N+:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[O-:18])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 660424-CyanobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 343062HCID 343062, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-cyanobenzaldehyde (392.9 mg, 3.00 mmol) and t-butylamine (227.3 mg, 3.10 mmol) in 1,2-dichloroethane (12 ml) was added sodium triacetoxyborohydride (0.8567 g, 4.04 mmol) and stirred for 3 hours. Acetic acid (0.17 ml, 2.95 mmol) was added to the mixture and stirred for 2.5 hours. The mixture was added to sat. NaHCO3 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated to give the crude title compound (595.3 mg).

Workup

  1. stirringstirred for 2.5 hours
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7617ff852cad4634a0e5bffaf26ef7ac
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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