Carbon Disulfide → Ethanedione, bis[4-(diethylamino)phenyl]-

HRID 373729Notes

Reaction equation

HRID 373729 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(=S)=S.[CH2:8]([N:10]([CH2:17][CH3:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9].[C:19](Cl)(=[O:23])[C:20](Cl)=[O:21]>C(Cl)(Cl)Cl.O>[CH2:17]([N:10]([CH2:8][CH3:9])[C:11]1[CH:16]=[CH:15][C:14]([C:19](=[O:23])[C:20]([C:14]2[CH:15]=[CH:16][C:11]([N:10]([CH2:17][CH3:18])[CH2:8][CH3:9])=[CH:12][CH:13]=2)=[O:21])=[CH:13][CH:12]=1)[CH3:18]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 7061N,N-DiethylanilineHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4616522Ethanedione, bis[4-(diethylamino)phenyl]-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To 11.6 g of anhydrous aluminum chloride, 60 ml of carbon disulfide was added, followed by dropwise addition of 30 g of N,N-diethylaniline under ice-cooling. Then, 10 g of oxalyl chloride was added dropwise thereto at 5° C. or lower, followed by the reaction for 1 hour with stirring. After the reaction, the reaction solution was poured into 100 ml of water and 200 ml of chloroform. The chloroform layer obtained by separation was washed with 2N hydrochloric acid, dried and concentrated. The residue was recrystallized from ethyl acetate to give yellow 1,2-bis(4-diethylaminophenyl)ethane-1,2-dione in an amount of 7.0 g.

Workup

  1. temperaturecooling
  2. customat 5° C. or lower, followed by the reaction for 1 hour
  3. customAfter the reaction
  4. washwas washed with 2N hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8959d6b050d3403d8fe73b18792e8747
Source dataset
uspto-grants-1992_11
Patent number
US05164512

Reaction notes

Loading…