Methyl iodide → 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile

HRID 840234

반응식

HRID 840234 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]#[N:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]([C:22]1[CH:23]=[C:24]([N:28]=[C:29]=[S:30])[CH:25]=[CH:26][CH:27]=1)#[N:21].[CH3:31]I>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11](=[C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([C:20]#[N:21])[CH:23]=2)[S:30][CH3:31])[C:12]#[N:13])(=[O:9])=[O:10])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 765783-Cyanophenyl isothiocyanateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrile

생성물 1

HCID 701506282-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile수율 96.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of 4-chlorophenylsulfonylacetonitrile (1.0 g, 4.64 mmol) in dry acetone (10 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-cyanophenyl isothiocyanate (0.78 g, 4.87 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 20 h. Excess of potassium carbonate was filtered off, methyl iodide (0.859 ml, 13.9 mmol) was added to the filtrate, and stirring was continued for 3 h. The mixture was evaporated and the residue was dissolved in dichloromethane and extracted with water and brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to afford 1.74 g (96%) of the title compound as golden brown crystals. Mp 168-170° C. 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 7.50-7.68 (m, 6H), 7.84-7.93(m, 2H),9.89 (br s, 1H).

후처리

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 3 h
  5. customThe mixture was evaporated
  6. dissolutionthe residue was dissolved in dichloromethane
  7. extractionextracted with water and brine
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-dd63cd7f73a14cf2b87747e6c506376d
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365609B1

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