Dimethylformamide → HCID 20563001, compound

HRID 613980Notes

Reaction equation

HRID 613980 reaction equation
N[C:2]1[O:3][C:4]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][C:5]=2[C:6](=[O:10])[C:7]=1C=O.[C:17]([CH2:19][C:20](Cl)=O)#[N:18].C[N:24]([CH3:27])C=O>>[CH2:15]([C:12]1[CH:11]=[C:5]2[C:4]([O:3][C:2]3[CH:20]=[C:19]([C:27]#[N:24])[CH:17]=[N:18][C:7]=3[C:6]2=[O:10])=[CH:14][CH:13]=1)[CH3:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 110515942-Cyanoacetyl chlorideHCID 126892482-Amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carbaldehyde

Product 1

HCID 20563001HCID 20563001, compound

Procedure

In 40 ml of dimethylformamide was dissolved 1.82 g of 2-amino-6-ethyl-4-oxo-4H-1-benzopyran-3-carboxaldehyde, followed by the addition of 3.5 g of cyanoacetyl chloride. The mixture was reacted at 60° C. for 3 hours, with constant stirring. The solvent was then distilled off under reduced pressure and the residue was chromatographed on silica gel. The desired product was recovered from the chloroform eluate and recrystallized from acetonitrile. By the above procedure was obtained 1.03 g of 7-ethyl-3-cyano-1-azaxanthone, m.p. 183°-185° C.

Workup

  1. customThe mixture was reacted at 60° C. for 3 hours, with constant stirring
  2. distillationThe solvent was then distilled off under reduced pressure
  3. customthe residue was chromatographed on silica gel
  4. customThe desired product was recovered from the chloroform eluate
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-647ff5ea3541436486f751158bb8f76d
Source dataset
uspto-grants-1979_03
Patent number
US04143042

Reaction notes

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