Sodium hydride → HCID 23047285, compound

HRID 2107135Notes

Reaction equation

HRID 2107135 reaction equation
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)#[N:2].[H-].[Na+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2C=C(S([O-])(=O)=O)C=C[C:29]=2C)=[CH:24][CH:23]=1>CN(C=O)C.C1(C)C=CC=CC=1>[C:1]([C:3]([C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)([CH2:29][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19738031HCID 19738031, compoundHCID 23047347HCID 23047347, compound

Product 1

HCID 23047285HCID 23047285, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Conditions

Temperature
5 °C

Procedure

1-Cyano-1-(4-chlorophenyl)-2-(3-pyridyl)ethane (4.0 gms, 0.0165 m) was placed in a 100 ml three neck flask, under a nitrogen atmosphere, equipped with a magnetic stirrer, thermometer, gas inlet tube and a cooling bath. To the flask was added 50 ml DMF-toluene (1:2), and the resulting solution was cooled to 5° C. Sodium hydride (0.4 gm, 0.018m of 60% NaH) was added and the mixture was stirred for 30 minutes. Then 4-methoxyphenyl-p-toluene-sulfonate (5.0 gm, 0.0165 m) was added and the mixture was stirred for 1 hour at 5° C., followed by stirring at room temperature for another 2 hours. The reaction mixture was quenched with water (10 ml), then placed in a separatory funnel using methylene chloride (200 ml) as a rinse. The organic layer of methylene chloride was washed with water (5×100 ml) and brine (100 ml), then dried. Solvent removal followed by column chromatographic purification afforded 3.6 gms of the titled compound.

Workup

  1. customequipped with a magnetic stirrer
  2. stirringthe mixture was stirred for 1 hour at 5° C.
  3. stirringby stirring at room temperature for another 2 hours
  4. customThe reaction mixture was quenched with water (10 ml)
  5. customplaced in a separatory funnel
  6. washThe organic layer of methylene chloride was washed with water (5×100 ml) and brine (100 ml)
  7. customdried
  8. customSolvent removal
  9. customfollowed by column chromatographic purification

Sources & evidence

ORD record
ord-69615ad1439743e0843d5a9b391645ea
Source dataset
uspto-grants-1990_06
Patent number
US04933339

Reaction notes

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