Hydrochloric Acid → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile

HRID 279087

반응식

HRID 279087 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+].[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([N:32]=[C:33]=[S:34])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.[C:37](=O)([O-])O.[Na+].CI.Cl>CC(C)=O.O>[F:29][C:28]([F:30])([F:31])[C:26]1[CH:25]=[C:24]([NH:32][C:33]([S:34][CH3:37])=[C:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[C:12]#[N:13])[CH:23]=[C:22]([C:21]([F:35])([F:20])[F:36])[CH:27]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 7358292-(4-Chlorobenzenesulfonyl)acetonitrileHCID 27333953,5-Bis(trifluoromethyl)phenyl isothiocyanate

생성물 1

HCID 865837313-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile수율 93.6%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

To a solution of 4-chlorophenylsulfonylacetonitrile (1.10 g, 5.10 mmol) in dry acetone (12 ml) first dry potassium carbonate (1.41 g, 10.2 mmol) and then 3,5-bis(trifluoromethyl)phenyl isothiocyanate (1,44 g, 5.31 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 1 h, and then filtered. To the filtrate a solution of sodium hydrogencarbonate (0.86 g) in water (15 ml) and methyl iodide (0.945 ml, 15.3 mmol) was added. The mixture was stirred at room temperature for 3.5 h. Then pH was adjusted to ˜4 with 1N HCl. The precipitate was filtered off and washed with water to give 2.39 g (93%) of the title compound. Recrystallisation could be done from ethyl acetate/heptane 1:3. Mp 150.5-152.5° C. 1H NMR (300 MHz, CDCl3): δ=2.25 (s, 3H), 7.57 (d, 2H), 7.79 (s, 2H), 7.83 (s, 1H), 7.88 (d, 2H), 10.0 (br s, 1H); MA calc for C18H11ClF6N2O2S2: C, 43.17%; H, 2.21%; N, 5.59%. Found: C, 43.25%; H, 2.16%; N, 5.59%.

후처리

  1. filtrationfiltered
  2. stirringThe mixture was stirred at room temperature for 3.5 h
  3. filtrationThe precipitate was filtered off
  4. washwashed with water

출처 및 근거

ORD 기록
ord-fad4d7cfa295418ca915b590471dc9be
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362205B1

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