Methyl iodide → 3-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

HRID 279134

반응식

HRID 279134 반응식
[CH3:1][S:2]([CH2:5][C:6]#[N:7])(=[O:4])=[O:3].[C:8](=O)([O-])[O-].[K+].[K+].[CH2:14]1[O:22][C:21]2[CH:20]=[CH:19][C:18]([N:23]=[C:24]=[S:25])=[CH:17][C:16]=2[O:15]1.CI>CC(C)=O>[O:22]1[C:21]2[CH:20]=[CH:19][C:18]([NH:23][C:24]([S:25][CH3:8])=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]#[N:7])=[CH:17][C:16]=2[O:15][CH2:14]1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75283(Methylsulfonyl)acetonitrileHCID 1235931,3-Benzodioxole, 5-isothiocyanato-

생성물 1

HCID 701495853-(Benzo[1,3]dioxol-5-ylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile수율 65.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A solution of methanesulfonylacetonitrile (2.85 g, 23.9 mmol) in dry acetone (50 ml) was stirred while dry potassium carbonate (6.61 g, 47.8 mmol) and 3,4-methylenedioxyphenyl isothiocyanate (4.50 g, 25.1 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 (4.43 ml, 71.8 mmol) was added to the filtrate, and stirring was continued for 4 h at 50° C. 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 4.88 g (65%) of the title compound as golden brown crystals. Mp 168-170° C.1H NMR (200 MHz, DMSO-d6): δ=2.30 (s, 3H), 3.33 (s, 3H), 6.06 (s, 2H), 6.79 (dd, 1H), 6.94 (d, 1H), 6.97 (d, 1H), 9.98 (br s, 1H).

후처리

  1. additionwere added
  2. filtrationExcess of potassium carbonate was filtered off
  3. stirringstirring
  4. waitwas continued for 4 h at 50° C
  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-27b4340d3d1442bdbf7c7fd30c7156c8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362205B1

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