Acetic Acid → HCID 54524751, compound

HRID 1030880Notes

Reaction equation

HRID 1030880 reaction equation
[CH3:1][N:2]([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[C:9]([O:12][C:13](=O)[CH3:14])(=O)C.[C:16](O)(=O)C>[Cl-].[Zn+2].[Cl-]>[C:5]([C:4](=[CH:16][CH:14]=[CH:13][O:12][CH3:9])[C:3]([N:2]([CH3:8])[CH3:1])=[O:7])#[N:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 2511432-Cyano-N,N-dimethylacetamide

Product 1

HCID 54524751HCID 54524751, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a 250 ml 3-necked R.B. flask was charged 50 g malonodialdehyde bis(dimethylacetal), 22.5 g N,N-dimethyl-2-cyanoacetamide, 60 g acetic anhydride, 0.5 g zinc chloride and 100 ml acetic acid. It was heated to reflux to distill off low boilers until the pot temperature reached 125° C. and head reached 110° C. and a total of 60 ml distillate was collected. GC analysis of the pot content showed disappearance of N,N-dimethyl-2-cyanoacetamide. The reaction mixture was filtered to remove zinc catalyst and then rotovapped. The pot residue was crystallized from a methanol in dry ice-acetone bath to afford 16 g (44.3%) of the title compound.

Workup

  1. temperatureIt was heated
  2. temperatureto reflux
  3. distillationto distill off low boilers until the pot temperature
  4. customreached 125° C.
  5. customreached 110° C.
  6. distillationa total of 60 ml distillate was collected
  7. filtrationThe reaction mixture was filtered
  8. customto remove zinc catalyst
  9. customThe pot residue was crystallized from a methanol in dry ice-acetone bath

Sources & evidence

ORD record
ord-99d2f050096a49e6b7a3c6df9198b0a0
Source dataset
uspto-grants-1992_04
Patent number
US05107057

Reaction notes

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