Carbon Dioxide → HCID 13034522, compound

HRID 2059207Notes

Reaction equation

HRID 2059207 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([CH2:13]C(O)=O)#[N:12].[NH:17]1CCC[CH2:19][CH2:18]1.C(=O)=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]([CH2:13][C:11]#[N:12])[CH2:19][C:18]#[N:17]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 67372,6-DichlorobenzaldehydeHCID 8082PiperidineHCID 9740Cyanoacetic acid

Product 1

HCID 13034522HCID 13034522, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution consisting of 31.5 grams (g) of 2,6-dichlorobenzaldehyde, 39 g of cyanoacetic acid and 2.5 milliliters (ml) of piperidine in 100 ml of pyridine is heated on a steambath for 7 hours. The initial rapid evolution of carbon dioxide gradually diminishes over the reaction time. Most of the solvent is removed under reduced pressure and the residue is dissolved in about 400 ml of benzene. The solution is washed three times with water, three times with dilute sodium bisulfite, again with water, and finally with saturated sodium bicarbonate. The solvent is removed under vacuum and the residue is recrystallized once from 50 ml of methanol and once more from 50 ml of isopropanol to give 12.3 g of 3-(2,6-dichlorophenyl)glutaronitrile having a melting point (mp) of 104°-6° C.

Workup

  1. temperatureis heated on a steambath for 7 hours
  2. customMost of the solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in about 400 ml of benzene
  4. washThe solution is washed three times with water, three times with dilute sodium bisulfite
  5. customThe solvent is removed under vacuum
  6. customthe residue is recrystallized once from 50 ml of methanol and once more from 50 ml of isopropanol

Sources & evidence

ORD record
ord-4e82890c4fa14af3a9ed74a0482e8c10
Source dataset
uspto-grants-1982_03
Patent number
US04322421

Reaction notes

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