Hydrochloric Acid → Ethyl 2,3-Dicyanopropionate

HRID 368550Notes

Reaction equation

HRID 368550 reaction equation
[C-:1]#[N:2].[K+].[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:5].[CH2:12]=O.[K].Cl>C(O)C.O>[C:4]([CH:6]([CH2:12][C:1]#[N:2])[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:5]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 7764Ethyl cyanoacetateHCID 9032Potassium CyanideHCID 5462222Potassium

Product 1

HCID 10725530Ethyl 2,3-DicyanopropionateYield 77.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Potassium cyanide (13.0 g, 0.2M) was stirred in absolute ethanol and ethyl cyanoacetate (22.6 g, 0.2M) and paraformaldehyde (6.0 g, 0.2m) were added at ambient temperature. After 5 minutes the white suspension was heated under reflux conditions for 12 minutes, and the orange solution was evaporated to dryness in vacuo at below 25° C. to give a buff solid. The solid (the potassium salt) was dissolved in water (400 ml), acidified to pH 5 with 2M hydrochloric acid solution, giving a red oil. This mixture was extracted with dichloromethane and the extracts dried and evaporated to dryness in vacuo to give the title compound as a red oil (23.5 g), 1H NMR (CDCl3) d 4.3 (2H, q), 3.95 (1H, t), 3.0 (2H, d), 1.35 (3H, t); identical with an authentic sample. Distilled material had b.p. 132-136° C. at 0.5mmHg. Yield : 77%.

Workup

  1. temperatureAfter 5 minutes the white suspension was heated under reflux conditions for 12 minutes
  2. customthe orange solution was evaporated to dryness in vacuo at below 25° C.
  3. customto give a buff solid
  4. customgiving a red oil
  5. extractionThis mixture was extracted with dichloromethane
  6. customthe extracts dried
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2c9b8d6c1a8b4e7fa5e8108fe76861e3
Source dataset
uspto-grants-2000_10
Patent number
US06133432

Reaction notes

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