Malononitrile → HCID 22714258, compound

HRID 351654Notes

Reaction equation

HRID 351654 reaction equation
[H-].[Na+].[CH2:3]([C:6]#[N:7])[C:4]#[N:5].[CH3:8][C:9]1[S:10][C:11](S(C)(=O)=O)=[N:12][N:13]=1>C1COCC1>[CH3:8][C:9]1[S:10][C:11]([CH:3]([C:6]#[N:7])[C:4]#[N:5])=[N:12][N:13]=1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 22714268HCID 22714268, compound

Product 1

HCID 22714258HCID 22714258, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
50 °C

Procedure

Under argon, 400 mg (10.0 mmol) of sodium hydride (60% suspension in oil) are suspended at room temperature in 40 ml of THF. A solution of 661 mg (10.0 mmol) of malonodinitrile in 10 ml of THF is added dropwise, and the reaction mixture is stirred for 15 min. A solution of 891 mg (5.0 mmol) of 2-methyl-5-methylsulphonyl-1,3,4-thiadiazole in 10 ml of THF is added dropwise. The reaction mixture is heated to 50° C. and stirred overnight, cooled and concentrated using a rotary evaporator. The residue is dissolved in water and adjusted to pH=3 using HCl. A brown solid precipitates out, and this solid is filtered off and dried under reduced pressure.

Workup

  1. stirringstirred overnight
  2. temperaturecooled
  3. concentrationconcentrated
  4. customa rotary evaporator
  5. dissolutionThe residue is dissolved in water
  6. customA brown solid precipitates out, and this solid
  7. filtrationis filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-7f150fb4aa00482d854c32916334f859
Source dataset
uspto-grants-2004_06
Patent number
US06743798B1

Reaction notes

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