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

HRID 279087

反応式

HRID 279087 の反応式
[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

参加物

9

反応物 6

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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%.

後処理

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

出典と根拠

ORDレコード
ord-fad4d7cfa295418ca915b590471dc9be
出典データセット
uspto-grants-2002_03
特許番号
US06362205B1

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