Sodium hydride → HCID 23510116, compound

HRID 1883143Notes

Reaction equation

HRID 1883143 reaction equation
[H-].[Na+].[CH:3]1[CH:8]=[CH:7][C:6]([C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][CH2:11][C:12]#[N:13])=[CH:5][CH:4]=1.[H][H].Cl[CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>C1COCC1.ClCCl>[C:9](=[N:10][CH:11]([CH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)[C:12]#[N:13])([C:6]1[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 745714-(Chloromethyl)pyridineHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 23510116HCID 23510116, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.54 g, 23 mmol) in anhydrous THF (80 mL) was added portionwise N-(diphenylmethylene)aminoacetonitrile (5.00 g, 23 mmol). The reaction was allowed to stir at room temperature until hydrogen evolution ceased and then cooled to 0° C. for 10 minutes. To the reaction mixture was added a solution of 4-chloromethyl pyridine (3.03 g, 24 mmol) in anhydrous THF (10 mL) and dichloromethane (3 mL). The reaction mixture was stirred at room temperature for 50 minutes and then cooled to 0° C. and was added saturated ammonium chloride (80 mL) and extracted with three 80 mL portions of ethyl acetate. The combined organic layers was dried on sodium sulfate and concentrated to give a viscous oil. Purification by column chromatography (40:60 ethyl acetate:hexane) and trituration with hexanes gave 2-(benzhydrylidene-amino)-3-pyridin-4-yl-propionitrile (4.02 g, 52%).

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with three 80 mL portions of ethyl acetate
  3. customThe combined organic layers was dried on sodium sulfate
  4. concentrationconcentrated
  5. customto give a viscous oil
  6. customPurification by column chromatography (40:60 ethyl acetate:hexane) and trituration with hexanes

Sources & evidence

ORD record
ord-f03c07ded8c94202b2cf0f95ea89a36d
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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