Diethyl Ether → HCID 19790383, compound

HRID 893102Notes

Reaction equation

HRID 893102 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH:9]([C:13]#[N:14])[C:10]([NH2:12])=[O:11])=O)=[CH:4][CH:3]=1.CCOCC.C(Cl)(Cl)[Cl:23]>>[Cl:23][C:13]1[NH:14][C:6]([C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:8][C:9]=1[C:10]([NH2:12])=[O:11]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 19790387HCID 19790387, compound

Product 1

HCID 19790383HCID 19790383, compoundYield 46%

Procedure

Into a mixture of 3-(p-chlorobenzoyl)-2-cyanopropionamide (1.0 g, 0.0042 mol), ether and chloro-form is bubbled dry hydrogen chloride for about 10 minutes. TLC shows no remaining 3-(p-chlorobenzoyl)-2-cyanopropionamide. Solvent is removed in vacuo and the residue is distributed between ethyl acetate and water. The organic phase is separated, washed with water and brine and dried over magnesium sulfate. Solvent is removed and the resulting solid is triturated with ether and collected to give the title compound as a light brown solid (0.50 g, 46%, mp >200° C.). Identified by IR and NMR spectral analyses.

Workup

  1. customis bubbled dry hydrogen chloride for about 10 minutes
  2. customSolvent is removed in vacuo
  3. customThe organic phase is separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customSolvent is removed
  7. customthe resulting solid is triturated with ether
  8. customcollected

Sources & evidence

ORD record
ord-7d5049f8b55a425dab3da019cebdccf2
Source dataset
uspto-grants-1992_06
Patent number
US05122615

Reaction notes

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