Sodium hydride → HCID 19738043, compound

HRID 2255368Notes

Reaction equation

HRID 2255368 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:11]#[N:12])=[CH:6][CH:5]=1.Cl[CH2:22][N:23]1[CH:27]=[N:26][CH:25]=[N:24]1>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:11]#[N:12])([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH2:22][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 37438821-Chloromethyl-1H-1,2,4-triazoleHCID 14304727HCID 14304727, compound

Product 1

HCID 19738043HCID 19738043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flask was added 0.24 g. (5.5 mmoles) of a 55% oil dispersion of sodium hydride. After washing the sodium hydride with hexane to remove the mineral oil, 25 ml. of DMF was added, the solution cooled to 0° C., and then 1.3 g. (5.0 mmoles) of 2-(4-chlorophenyl)-4-(4-morpholinyl)butyronitrile in 15 ml. of DMF was slowly added. The solution was stirred for 30 minutes and then 0.59 g. (5.0 mmoles) of 1-(chloromethyl)-1,2,4-triazole in 10 ml. of DMF was added slowly. The reaction was stirred overnight at room temperature and then was poured into ice water. The organics were extracted into ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated. The product was purified using chromatography by eluting the impurities with ethyl acetate and the desired 1-[2-(4-chlorophenyl)-2-cyano-4-(4-morpholinyl)butyl]-1,2,4-triazole product with acetone to give 1.0 g. (58% yield) of an orange oil.

Workup

  1. additionTo a flask was added 0.24 g
  2. washAfter washing the sodium hydride with hexane
  3. customto remove the mineral oil, 25 ml
  4. additionof DMF was added
  5. stirringThe reaction was stirred overnight at room temperature
  6. extractionThe organics were extracted into ethyl acetate
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was purified
  12. washby eluting the impurities with ethyl acetate

Sources & evidence

ORD record
ord-4d0029a5b48247b1b8a83d93f5ffd3a1
Source dataset
uspto-grants-1993_08
Patent number
US05240925

Reaction notes

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