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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
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* Storage: {[proInfo.prStorage]}
CAS No. : | 1851-09-8 | MDL No. : | MFCD00045626 |
Formula : | C8H6ClNO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HAQGVGPNKGGSMK-UHFFFAOYSA-N |
M.W : | 215.66 g/mol | Pubchem ID : | 735829 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 49.1 |
TPSA : | 66.31 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.5 cm/s |
Log Po/w (iLOGP) : | 1.11 |
Log Po/w (XLOGP3) : | 1.57 |
Log Po/w (WLOGP) : | 2.72 |
Log Po/w (MLOGP) : | 1.47 |
Log Po/w (SILICOS-IT) : | 1.62 |
Consensus Log Po/w : | 1.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.38 |
Solubility : | 0.908 mg/ml ; 0.00421 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.57 |
Solubility : | 0.577 mg/ml ; 0.00267 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.44 |
Solubility : | 0.079 mg/ml ; 0.000366 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.23 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501 | UN#: | 3439 |
Hazard Statements: | H301+H311+H331-H315-H319 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 56% 2: 29% | In 1,4-dioxane for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With hydrogenchloride In 1,4-dioxane for 8h; | |
50% | With hydrogenchloride In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | at 100℃; for 0.0666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydrogencarbonate In ethanol; toluene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) Na, (ii) /BRN= 471392/, (iii) aq. HCl; Multistep reaction; | ||
With sodium ethanolate In 1,4-dioxane; ethanol for 44h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With acetic anhydride; zinc(II) chloride at 125 - 130℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With acetic anhydride at 140℃; for 7h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | Stage #1: pyridin-3-yl isothiocyanate; 2-(4-chlorobenzenesulfonyl)acetonitrile With potassium carbonate In acetone at 20℃; for 4h; Stage #2: methyl iodide In acetone at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3,5-dichlorophenylisothiocyanate With potassium carbonate In acetone at 20℃; for 17h; Stage #2: methyl iodide In acetone at 20℃; for 0.75h; | |
1.42 g (72%) | With potassium carbonate In acetone | 7.1 1 1 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-methylsulfanyl-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,5-dichlorophenyl isothiocyanate (0.99 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 45 min.. Then pH was adjusted to 1 with 1N aqueous HCl. The precipitate was filtered off and washed with water to give 1.86 g (93%) of a crude product. Recrystallisation from ethyl acetate/heptane (1:1) gave 1.42 g (72%) of the title compound contaminated with 4-chlorophenylsulfonylacetonitrile. Mp 128-131° C. 1H NMR (200 MHz, CDCl3): δ=2.25 (s, 3H), 7.20 (d, 2H), 7.30 (t, 1H), 7.55 (d, 2H), 7.85 (d, 2H), 9.80 (br s, 1H); El SP/MS: 434 (M+), 436 (M+2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 20% | Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3,5-bistrifluoromethylphenylisothiocyanate With potassium carbonate In acetone at 20℃; for 2h; Stage #2: methyl iodide In acetone at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3,5-bistrifluoromethylphenylisothiocyanate With potassium carbonate In acetone at 20℃; for 4.5h; Stage #2: methyl iodide In acetone at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 1-isothiocyanato-3,5-dimethoxybenzene With potassium carbonate In acetone at 20℃; for 2.25h; Stage #2: methyl iodide In acetone at 20℃; for 4h; | |
1.27 g (65%) | With potassium carbonate In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetone | 10.1 1 1 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanyl-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 9, 9.3 mmol) and then 3,5-dimethoxyphenyl isothiocyanate (0.96 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 2 h 15 min and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 4 h. The reaction mixture was concentrated. The residue was dissolved in DCM, washed with water, dried (Na2SO4) and concentrated. The residue was crystallized from ethyl acetate/heptane 1:2 to give 1.27 g (65%) of the title compound. Mp 119.5-123° C.; 1H NMR (200 MHz, CDCl3): δ=2.29 (s, 3H), 3.80 (s, 6H), 3.36 (m, 3H), 7.53 (d, 2H), 7.87 (d, 2H), 9.82 (br s, 1H); El SP/MS: 424 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 5-isothiocyanato-benzo[1,3]dioxole With potassium carbonate In acetone at 20℃; for 60h; Stage #2: methyl iodide In acetone at 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With pyridine for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With pyridine for 10h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium bis(permanganate); acetic acid In acetonitrile at 20℃; for 0.0333333h; | |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; | ||
With dihydrogen peroxide; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 89 percent / K2CO3 / dimethylformamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C 3: 63 percent / POCl3 / 2 h / 60 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / pyridine / 10 h / Heating 2: 89 percent / K2CO3 / dimethylformamide / 20 °C 3: 59 percent / POCl3 / 2 h / 60 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C 3: 58 percent / POCl3 / 2 h / 60 - 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ZnCl2, Ac2O / 120 - 130 °C 2: NH3 / tetrahydrofuran | ||
Multi-step reaction with 2 steps 1: AcOH / Heating 2: NH3 / ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4 h / 20 °C 1.2: 16 percent / acetone / 16 h / 20 °C 2.1: 58 percent / 22 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 17 h / 20 °C 1.2: 86 percent / acetone / 0.75 h / 20 °C 2.1: 60 percent / 22 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 2.25 h / 20 °C 1.2: 65 percent / acetone / 4 h / 20 °C 2.1: 36 percent / acetonitrile / 17 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 17 h / 20 °C 1.2: 86 percent / acetone / 0.75 h / 20 °C 2.1: 17 percent / 40 h / 50 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 17 h / 20 °C 1.2: 86 percent / acetone / 0.75 h / 20 °C 2.1: 49 percent / acetonitrile / 40 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 2.25 h / 20 °C 1.2: 65 percent / acetone / 4 h / 20 °C 2.1: 83 percent / acetonitrile / 17 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 60 h / 20 °C 1.2: 94 percent / acetone / 1.5 h / 20 °C 2.1: 26 percent / 17 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.5 h / 20 °C 1.2: 82 percent / acetone / 2 h / 20 °C 2.1: 65 percent / 19 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.5 h / 20 °C 1.2: 82 percent / acetone / 2 h / 20 °C 2.1: 55 percent / 18 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.5 h / 20 °C 1.2: 82 percent / acetone / 2 h / 20 °C 2.1: 48 percent / 17 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.5 h / 20 °C 1.2: 82 percent / acetone / 2 h / 20 °C 2.1: 11 percent / 20 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 68 percent / pyridine / acetonitrile / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 68 percent / pyridine / acetonitrile / 0.5 h / Heating 3: 75 percent / N-bromosuccinimide / CH2Cl2 / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 68 percent / pyridine / acetonitrile / 0.5 h / Heating 3: 71 percent / acetic anhydride; acetyl nitrate / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 78 percent / pyridine / acetonitrile / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 78 percent / pyridine / acetonitrile / 18 h / 20 °C 3: 85 percent / N-bromosuccinimide / CH2Cl2 / 0.75 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 78 percent / pyridine / acetonitrile / 18 h / 20 °C 3: 56 percent / iodine; silver nitrate / acetonitrile / 0.33 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 82 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / ethanol / 16 h / 20 °C 2: 60 percent / pyridine / acetonitrile / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1. sodium bicarbonate / 1. ethanol, toluene, reflux, 1 h; 2. reflux, 1.5 h 2: 68 percent / 1percent NaOH / H2O / 1 h / 80 °C | ||
Multi-step reaction with 2 steps 1: aq. ethanol; toluene / 1 h / Heating 2: 68 percent / NaOH / aq. ethanol / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium azide; triethylamine hydrochloride In DMF (N,N-dimethyl-formamide) at 80℃; for 16h; | 192 Example 192: 5-(4-Chlorobenzenesulfonylmethyl)-1H-tetrazole Example 192: 5-(4-Chlorobenzenesulfonylmethyl)-1H-tetrazole To an N,N-dimethylformamide (100 ml) solution of 4-chlorophenylsulfonylacetonitrile (2.81 g, 13.0 mmol) and triethylamine hydrochloride (4.24 g, 65.2 mmol) was added sodium azide (10.8 g, 78.2 mmol) and the mixture was stirred at 80°C for 16 hours.. The reaction mixture was then cooled to room temperature.. ethyl acetate was added and the mixture was washed with a saturated aqueous solution of ammonium chloride.. The organic layer was dried over anhydrous sodium sulfate.. After filtration, the filtrate was concentrated under reduced pressure.. The resulting solid was washed with diethyl ether and then, collected by filtration, whereby the title compound (2.53 g, 9.78 mmol, 75%) was obtained as a white solid.1H-NMR (400MHz, CD3OD) δ: 5.02(2H,s), 7.62(1H,d,J=8.6Hz), 7.73(2H,d,J=8.6Hz). MS m/z: 300 (M++H+CH3CN). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2% | With ammonium acetate In toluene for 12h; Heating / reflux; | 7.A Example 7 (General procedure (B)); (E/Z)-2- (4-CHLORO-BENZENESULFONYL)-3- (3, 5-DI-TERT-BUTYL-4-HYDROXY-PHENYL)-BUT-2- enenitrile; Step A To a solution of the appropriate carbonylcompound I (1 mmole) in toluene 10 ML, the appropriate SULFONYLCOMPOUND 11 (1 MMOLE) and ammonium acetate (1 MMOLE) was added. The reaction mixture was heated at reflux for 12 hours with continuous separation of water. The products III were isolated either by Step A: Aquae's work up followed by column chromatography or Step C: Aqua's work up followed by CRYSTALLISATION; The title compound was prepared from 3, 5-di-tert-butyl-hydroxyacetophenone and 4- CHLORO-BENZENESULFONYL ACETONITRILE in 2 % yield. 'H NMR (CDCI3) : (E) S ppm 1.43 (s, 18 H) 2.69 (s, 3 H) 5.66 (m, 1 H) 7.33 (s, 2 H) 7.59 (d, J=9.04 Hz, 2 H) 8.00 (d, J=8.67 Hz, 2 H) ;'H NMR (CDCI3) : (Z) 3 ppm 1.41 (s, 18 H) 2.51 (m, 3 H) 5.55 (s, 1 H) 6.92 (s, 2 H) 7.26 (d, 2 H) 7.39 (d, 2 H); HPLC-MS (Method A): m/z = 468 (M+23); Rt = 5.6 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With piperidine In ethanol for 12h; Heating / reflux; | 1 To a solution of the appropriate carbonylcompound (1 mmole) in ethanol 4 ml, the appropriate activated methylen compound (1 mmole) and a catalytic amount of piperidine (0.1 mmole) was added. The reaction mixture was heated at reflux for12 hours. The products were isolated either by, Step A: cooling filtration and crystallisation or Step B: Evaporation of solvent followed by column chromatography |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With piperidine In ethanol at 80℃; for 12h; | 1 Example 1; 2-(4-Chlorobenzenesulfonyl)-3-(1 H-indol-5-yl)acrylonitrile; 5-Formylindole (250 mg, 1.72 mmol) was dissolved in ethanol 3 ml, and 4- chlorophenylsulfonylacetonitrile (557 mg, 2.58 mmol), and piperidine (0.009 ml, 0.09 mmol) were added. The mixture was stirred at 80 °C for 12 hours. The reaction mixture was allowed to cool to room temperature, and a yellow powder was collected by filtration. The powder was washed with cold ethanol, and dried to afford 523 mg of the title compound in 88% yield. ¹H NMR (DMSO-d6) : No. ppm: 6.66 (s, 1 H) 7.54 (dd, 1 H) 7.60 (d, 1 H) 7.82 (d, 2 H) 7.86 (dd, 1 H) 8.03 (d, 2 H) 8.37 (s, 1 H) 8.55 (s, 1 H) 11.79 (br s, 1 H) ; HPLC-MS (Method A): m/z = 343 (M+1 ), 365 (M+23) ; Rt = 4.322 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
294 mg (16%) | With potassium carbonate In ethyl acetate; acetone | 6.1 1 1 2-(4-Chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.6 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then pyridin-3-yl isothiocyanate (0.663 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.315 ml, 5.1 mmcl) was added. The mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated and the residue was taken up into ethyl acetate and water. The organic layer was washed with 1N aqueous HCl (2X). The organic phase was dried (sodium sulfate) and concentrated. The residue was purified by flash chromatography using heptanelethyl acetate 1:2 as eluent and recrystallisation in ethyl acetate to give 294 mg (16%) of the title compound. Mp 181-182° C. 1H NMR (300 MHz, CDCl3): δ=2.20 (s, 3H), 7.36 (dd, 1H), 7.54 (dm, 2H), 7.6 (m, 1H), 7.88 (dm, 2H), 8.55 (m, 2H), 9.85 (br s, 1H); El SP/MS: 365 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.12 g (59%) | With potassium carbonate In acetone | 8.1 1 1 3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.64 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,4-methylenedioxyphenyl isothio-cyanate (0.87 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 50 min.. Then pH was adjusted to 1 with 1N aqueous HCl. The precipitate was filtered off and washed with water to give 1.12 g (59%) of the title compound. Mp 196-200° C. 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 6.05 (s, 2H), 6.68 (m, 2H), 6.80 (d, 1H), 7.53 (d, 2H), 7.87 (d, 2H), 9.80 (br s, 1H); El SP/MS: 408 (M+). |
1.12 g (59%) | With potassium carbonate In acetone | 27.1 1 1 3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.00 g, 4.64 mmol) in dry acetone (10 ml) first dry potassium carbonate (1.28 g, 9.3 mmol) and then 3,4-methylenedioxyphenyl isothiocyanate (0.87 g, 4.9 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen for 4 h, and then filtered. To the filtrate methyl iodide (0.86 ml, 13.9 mmol) was added. The mixture was stirred at room temperature for 50 min.. Then pH was adjusted to 1 with 1N aqueous HCl. The precipitate was filtered off and washed with water to give 1.12 g (59%) of the title compound. Mp 196-200° C. (decomp.); 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 6.05 (s, 2H), 6.68 (m, 2H), 6.80 (d, 1H), 7.53 (d, 2H), 7.87 (d, 2H), 9.80 (br s, 1H); El SP/MS: 408 (M+). |
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2-((3,4-Dichlorophenyl)sulfonyl)acetonitrile
Similarity: 0.94
[ 87475-56-7 ]
2-((2-Chlorophenyl)sulfonyl)acetonitrile
Similarity: 0.92
[ 87475-64-7 ]
2-((2,4-Dichlorophenyl)sulfonyl)acetonitrile
Similarity: 0.91
[ 7205-80-3 ]
1-Chloro-4-(ethylsulfonyl)benzene
Similarity: 0.88
[ 98557-04-1 ]
2-((3,4-Dichlorophenyl)sulfonyl)acetonitrile
Similarity: 0.94
[ 87475-56-7 ]
2-((2-Chlorophenyl)sulfonyl)acetonitrile
Similarity: 0.92
[ 87475-64-7 ]
2-((2,4-Dichlorophenyl)sulfonyl)acetonitrile
Similarity: 0.91
[ 63923-60-4 ]
2-((4-Chlorophenyl)sulfinyl)acetonitrile
Similarity: 0.90
[ 918803-95-9 ]
2-((3-Chloro-4-fluorophenyl)sulfonyl)acetonitrile
Similarity: 0.86