Dimethylformamide → HCID 86748203, compound

HRID 1708588Notes

Reaction equation

HRID 1708588 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]([CH3:11])[CH:9]=O.[CH3:12][N:13]([CH3:18])/[CH:14]=[CH:15]/[C:16]#[N:17].O.O.[C:21]([OH:26])(=[O:25])[C:22]([OH:24])=[O:23]>ClCCCl.CC(O)C>[C:21]([O-:26])(=[O:25])[C:22]([O-:24])=[O:23].[C:16]([C:15](=[CH:14][N:13]([CH3:18])[CH3:12])[CH:9]=[N+:8]([CH3:11])[CH3:7])#[N:17].[C:16]([C:15](=[CH:14][N:13]([CH3:18])[CH3:12])[CH:9]=[N+:8]([CH3:11])[CH3:7])#[N:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 61373Oxalic acid dihydrateHCID 65578Oxalyl chlorideHCID 53247353-Dimethylaminoacrylonitrile

Product 1

HCID 86748203HCID 86748203, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent3×HCID 3776IsopropanolSolvent2×

Procedure

A solution of oxalyl chloride (13.1 mL, 0.15 mol) in 1,2-dichloroethane is added dropwise to a solution of N,N-dimethylformamide (11.6 mL, 0.15 mol) in 1,2-dichloroethane while maintaining the reaction mixture temperature below 0° C. The reaction mixture is stirred for 45 minutes, treated with a solution of trans-3-dimethylaminoacrylonitrile (16.4 mL, 0.15 mol) in 1,2-dichloroethane, stirred at room temperature for 16 hours, refluxed for two hours and concentrated in vacuo to obtain a semi-solid residue. A solution of the residue in 2-propanol is treated with a solution of oxalic acid dihydrate (18.9 g, 0.15 mol) in 2-propanol and warmed until a clear solution is obtained. The clear solution is cooled to and held at room temperature for several hours, cooled in a freezer for two hours and filtered. The filter cake is washed sequentially with 2-propanol and ether and dried in a vacuum desiccator at 50° to give the title product (28.6 g, 79%).

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 0° C
  2. stirringstirred at room temperature for 16 hours
  3. temperaturerefluxed for two hours
  4. concentrationconcentrated in vacuo
  5. customto obtain a semi-solid residue
  6. temperaturewarmed until a clear solution
  7. customis obtained
  8. temperatureThe clear solution is cooled to and
  9. waitheld at room temperature for several hours
  10. temperaturecooled in a freezer for two hours
  11. filtrationfiltered
  12. washThe filter cake is washed sequentially with 2-propanol and ether
  13. customdried in a vacuum desiccator at 50°

Sources & evidence

ORD record
ord-bf78782cf64f4be3bbe81445ac34a6ae
Source dataset
uspto-grants-1994_10
Patent number
US05359089

Reaction notes

Loading…