Hydrochloric Acid → [Cyclohexyl(hydroxy)methylidene]propanedinitrile

HRID 915910Notes

Reaction equation

HRID 915910 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[CH:8]1([C:14](Cl)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl>O1CCCC1>[CH:8]1([C:14]([OH:15])=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 24758Sodium hydrideHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 23024290[Cyclohexyl(hydroxy)methylidene]propanedinitrileYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 60 ml tetrahydrofuran solution of 3.96 g (0.06 mol) of malononitrile, 4.8 g (60% in oil, 0.12 mol) of sodium hydride was added at 0° C. in four divided portions, and the mixture was stirred for 30 minutes at 0° C. Then, cyclohexanecarboxylic acid chloride was added dropwise, and the mixture was stirred for 30 minutes at room temperature. Then, 150 ml of 1M hydrochloric acid was slowly added, and the mixture was extracted with ethyl acetate. Then, the extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Recrystallization of the residue from diisopropyl ether gave 8.16 g (77%) of the captioned compound.

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThen, the extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customRecrystallization of the residue from diisopropyl ether

Sources & evidence

ORD record
ord-898f6f5faf2f495e85e3303da22f1b6f
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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