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

HRID 373732

반응식

HRID 373732 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f940ba0a035943f89c458d4521051fe5
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05164512

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