Cyanoacetamide → HCID 20400737, compound

HRID 1980809Notes

Reaction equation

HRID 1980809 reaction equation
CN([CH:4]=[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=O)C.[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].C[O-].[Na+]>CN(C)C=O.C(#N)C>[C:16]([C:18]1[C:19](=[O:20])[NH:21][C:6]2[CH2:7][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]=2[CH:4]=1)#[N:17]

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 539804411-[(Dimethylamino)methylidene]-3,4-dihydronaphthalen-2(1H)-one

Product 1

HCID 20400737HCID 20400737, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Heat 11.4 g of 1-dimethylaminomethylene-2-tetralone, 4.46 gm of cyanoacetamide and 6.6 gm of sodium methoxide in 100 ml of dimethylformamide for 8 hours at 80°. Cool and dilute the reaction mixture with 150 ml of acetonitrile. Remove the tan solid by filtration. Dissolve the solid in hot water and filter the mixture. Acidify this aqueous solution with concentrated hydrochloric acid to give a tan precipitate. Filter and wash the tan solid with chloroform to give the title compound, m.p. 301°-3°. Concentrate the remaining dimethylformamide:acetonitrile solution in vacuo to give a green-black residue and chromatograph on 800 ml of silica gel using cloroform:methanol 98:2 as eluant to give an additional amount the title compound.

Workup

  1. temperatureCool
  2. customRemove the tan solid
  3. filtrationby filtration
  4. dissolutionDissolve the solid in hot water
  5. filtrationfilter the mixture
  6. customto give a tan precipitate
  7. filtrationFilter
  8. washwash the tan solid with chloroform

Sources & evidence

ORD record
ord-4f69650b73eb40b991900d735ff7681a
Source dataset
uspto-grants-1985_04
Patent number
US04511569

Reaction notes

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