Acetonitrile → HCID 69720143, compound

HRID 896390Notes

Reaction equation

HRID 896390 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][CH:26]=[C:27]([CH:28]=O)[C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2].[OH-].[K+].[Cl-].[NH4+].[C:35](#[N:37])[CH3:36]>>[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][CH:26]=[C:27]([CH:28]=[CH:36][C:35]#[N:37])[C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 22349276HCID 22349276, compound

Product 1

HCID 69720143HCID 69720143, compoundYield 48%

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-4-carbaldehyde (237 mg, 0.586 mmol) and powdered KOH (33 mg, 0.59 mmol) in acetonitrile (10 mL) was heated at 70° C. for 1.5 hr. After cooling to ambient temperature saturated ammonium chloride was added followed by the removal of acetonitrile at reduced pressure. The residue was extracted with ethyl acetate (2×15 mL) and the combined organic phases washed with water, brine and dried (MgSO4). Purification by flash chromatography (eluent hexane:ethyl acetate 2:1) afforded 3-[2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-4-yl]-acrylonitrile (120 mg, 48%) as an off white foam:

Workup

  1. additionwas added
  2. customfollowed by the removal of acetonitrile at reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (2×15 mL)
  4. washthe combined organic phases washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customPurification by flash chromatography (eluent hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-3e844bea1ece41629be0c27554445b37
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

Loading…