Tetrahydrofuran → HCID 23510307, compound

HRID 1883147Notes

Reaction equation

HRID 1883147 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:22][C:23]1[C:28](COS(C)(=O)=O)=[CH:27][CH:26]=[CH:25][N:24]=1.[Cl-].[NH4+].[CH2:37]1COCC1>>[C:9](=[N:10][CH:11]([CH2:37][C:27]1[CH:26]=[CH:25][N:24]=[C:23]([Cl:22])[CH:28]=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

7

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 612957[(Diphenylmethylene)amino]acetonitrileHCID 715202573-Pyridinemethanol, 2-chloro-, 3-methanesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 23510307HCID 23510307, compoundYield 52%

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (0.34 g, 14 mmol) in anhydrous THF (80 mL) was added portionwise N-(diphenylmethylene)aminoacetonitrile (3.13 g, 14 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 methansulfonic acid 2-chloro-pyridinylmethyl ester (3.00 g, 13 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at room temperature for 20 minutes and then cooled to 0° C. and was added saturated ammonium chloride (50 mL) and extracted with three 100 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-(2-chloro-pyridin-4-yl)-propionitrile (4.02 g, 52%).

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with three 100 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-09b61d696da442e2afc57953a4df0877
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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