Carbon Disulfide → 1,2-Bis(4-diethylamino-2-methylphenyl)ethane-1,2-dione

HRID 373732

Reaction equation

HRID 373732 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(=S)=S.[CH2:8]([N:10]([CH2:18][CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)[CH3:9].[C:20](Cl)(=[O:24])[C:21](Cl)=[O:22]>C(Cl)(Cl)Cl.O>[CH2:18]([N:10]([CH2:8][CH3:9])[C:11]1[CH:16]=[CH:15][C:14]([C:20](=[O:24])[C:21]([C:14]2[CH:15]=[CH:16][C:11]([N:10]([CH2:18][CH3:19])[CH2:8][CH3:9])=[CH:12][C:13]=2[CH3:17])=[O:22])=[C:13]([CH3:17])[CH:12]=1)[CH3:19]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 65578Oxalyl chlorideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 137821031,2-Bis(4-diethylamino-2-methylphenyl)ethane-1,2-dioneYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To 8.3 g of anhydrous aluminum chloride, 30 ml of carbon disulfide was added, followed by dropwise addition of 16.3 g of N,N-diethyl-m-toluidine under ice-cooling. Then, 5 g of oxalyl chloride was added dropwise thereto at 5° C. or lower, and reacted for 1 hour with stirring. After the reaction, 50 ml of water and 100 ml of chloroform were added to the reaction solution. The chloroform layer obtained by separation was washed with 2N hydrochloric acid, dried and concentrated. The residue was recrystallized from ethyl acetate to yield 3.5 g of yellow 1,2-bis(4-diethylamino-2-methylphenyl)ethane-1,2-dione.

Workup

  1. temperaturecooling
  2. customat 5° C. or lower, and reacted for 1 hour
  3. additionwere added to the reaction solution
  4. washwas washed with 2N hydrochloric acid
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f940ba0a035943f89c458d4521051fe5
Source dataset
uspto-grants-1992_11
Patent number
US05164512

Linked notes

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