Cyanoacetamide → HCID 19790387, compound

HRID 893101Notes

Reaction equation

HRID 893101 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].O1CCCC1.CC(C)([O-])C.[K+].[Cl:18][C:19]1[CH:28]=[CH:27][C:22]([C:23](=[O:26])[CH2:24]Br)=[CH:21][CH:20]=1>O.[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C>[Cl:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([CH2:24][CH:3]([C:1]#[N:2])[C:4]([NH2:6])=[O:5])=[O:26])=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 7898CyanoacetamideHCID 8028TetrahydrofuranHCID 68303p-Chlorophenacyl bromide2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 19790387HCID 19790387, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred mixture of cyanoacetamide (2.5 g, 0.030 mol) and tetrahydrofuran (160 mL) is slowly added potassium tert-butoxide (3.3 g, 0.030 mol) followed by p-chlorophenacyl bromide (7.0 g, 0.030 mol). The reaction is slightly exothermic and, after a short time, TLC shows none of the p-chlorophenacyl bromide present. The reaction mixture is diluted with water and brine and extracted with ether. The ether extract is dried and concentrated in vacuo to give a red oil. Upon addition of a hexane/ethyl acetate mixture (3:1) to the oil a solid forms and is collected by filtration to give the title product as a light yellow solid (1.4 g, 20%, mp 160°-161° C.) which is identified by IR and NMR spectral analyses.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. customis dried
  4. concentrationconcentrated in vacuo
  5. customto give a red oil
  6. filtrationis collected by filtration

Sources & evidence

ORD record
ord-d86ca1e9c86a451293f0244167be8c7d
Source dataset
uspto-grants-1992_06
Patent number
US05122615

Reaction notes

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