Hydrochloric Acid → HCID 11022008, compound

HRID 2372919Notes

Reaction equation

HRID 2372919 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[Cl:17])[C:6](=O)[CH2:7][CH:8]([C:11]#[N:12])[C:9]#[N:10].CCOCC>C(Cl)(Cl)Cl>[Cl:1][C:9]1[NH:10][C:6]([C:5]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:3]([Cl:2])[CH:4]=2)=[CH:7][C:8]=1[C:11]#[N:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10857979Propanedinitrile, [2-(3,4-dichlorophenyl)-2-oxoethyl]-

Product 1

HCID 11022008HCID 11022008, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Hydrogen chloride gas is bubbled through a mixture of (3,4-dichlorophenacyl)malononitrile (8.3 g, 0.333 mol), ether (150 mL) and chloroform (100 mL) at a moderate rate, keeping the reaction mixture temperature below 35°-40° C. After 25 minutes, TLC shows the reaction is complete by UV analysis. The brown reaction mixture is poured into an ice-water mixture and extracted with ether. The combined organic extracts are washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a brown solid. The brown solid is washed with methylene chloride and filtered to give the title product as an off-white solid (6.7 g, 76%, mp >200° C.). Identified by IR and NMR spectral analyses.

Workup

  1. customthe reaction mixture temperature below 35°-40° C
  2. extractionextracted with ether
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a brown solid
  7. washThe brown solid is washed with methylene chloride
  8. filtrationfiltered

Sources & evidence

ORD record
ord-c06ff4c5cf32422da2f7dc22cb84eeb8
Source dataset
uspto-grants-1992_03
Patent number
US05101042

Reaction notes

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