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[ CAS No. 1851-09-8 ]

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3d Animation Molecule Structure of 1851-09-8
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Product Details of [ 1851-09-8 ]

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 :

Calculated chemistry of [ 1851-09-8 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.23

Safety of [ 1851-09-8 ]

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:
GHS Pictogram:

Application In Synthesis of [ 1851-09-8 ]

* 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.

  • Downstream synthetic route of [ 1851-09-8 ]

[ 1851-09-8 ] Synthesis Path-Downstream   1~58

  • 1
  • [ 1851-09-8 ]
  • [ 80410-57-7 ]
  • α-(4-chloro-benzenesulfonyl)-3-methoxy-4-nitro-cinnamonitrile [ No CAS ]
  • 2
  • [ 4651-91-6 ]
  • [ 1851-09-8 ]
  • [ 128277-21-4 ]
  • [ 128277-22-5 ]
YieldReaction ConditionsOperation in experiment
1: 56% 2: 29% In 1,4-dioxane for 12h; Ambient temperature;
  • 3
  • [ 4506-71-2 ]
  • [ 1851-09-8 ]
  • [ 91225-80-8 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogenchloride In 1,4-dioxane for 8h;
50% With hydrogenchloride In 1,4-dioxane
  • 5
  • [ 1851-09-8 ]
  • [ 52217-02-4 ]
  • [ 113525-47-6 ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydrogencarbonate In ethanol; toluene for 1h; Heating;
  • 6
  • [ 1851-09-8 ]
  • [ 103-72-0 ]
  • [ 25979-68-4 ]
YieldReaction ConditionsOperation in experiment
(i) Na, (ii) /BRN= 471392/, (iii) aq. HCl; Multistep reaction;
With sodium ethanolate In 1,4-dioxane; ethanol for 44h; Ambient temperature;
  • 7
  • [ 110-52-1 ]
  • [ 1851-09-8 ]
  • 1-(4-Chloro-benzenesulfonyl)-cyclopentanecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h;
  • 8
  • [ 111-24-0 ]
  • [ 1851-09-8 ]
  • 1-(4-Chloro-benzenesulfonyl)-cyclohexanecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h;
  • 9
  • [ 1851-09-8 ]
  • [ 106-93-4 ]
  • 1-(4-Chloro-benzenesulfonyl)-cyclopropanecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h;
  • 10
  • [ 1851-09-8 ]
  • [ 109-64-8 ]
  • 1-(4-Chloro-benzenesulfonyl)-cyclobutanecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 3h;
  • 11
  • [ 1445-45-0 ]
  • [ 1851-09-8 ]
  • [ 243984-82-9 ]
YieldReaction ConditionsOperation in experiment
68% With acetic anhydride; zinc(II) chloride at 125 - 130℃;
  • 12
  • [ 1851-09-8 ]
  • [ 707-07-3 ]
  • 2-(4-chlorophenylsulfonyl)-3-methoxy-3-phenylacrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With acetic anhydride at 140℃; for 7h;
  • 13
  • [ 40018-26-6 ]
  • [ 1851-09-8 ]
  • [ 360071-45-0 ]
YieldReaction ConditionsOperation in experiment
82% With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol at 20℃; for 16h;
  • 14
  • [ 17452-27-6 ]
  • [ 1851-09-8 ]
  • [ 74-88-4 ]
  • 2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 15
  • [ 1851-09-8 ]
  • [ 6590-93-8 ]
  • [ 74-88-4 ]
  • 2-(4-chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-methylsulfanylacrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 16
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 74-88-4 ]
  • 3-[N-[3,5-bis(trifluoromethyl)phenyl]-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-methylsulfanylacrylonitrile [ No CAS ]
  • N-[3,5-bis(trifluoromethyl)phenyl]-2-(4-chlorobenzenesulfonyl)-2-cyano-2-methylthioacetimidic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 17
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 74-88-4 ]
  • 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-methylsulfanylacrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 18
  • [ 1851-09-8 ]
  • [ 104968-58-3 ]
  • [ 74-88-4 ]
  • 2-(4-chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-methylsulfanylacrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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+).
  • 19
  • [ 1851-09-8 ]
  • [ 113504-93-1 ]
  • [ 74-88-4 ]
  • 3-(benzo[1,3]dioxol-5-ylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanylacrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 20
  • [ 1851-09-8 ]
  • [ 21087-64-9 ]
  • 7-amino-3-<i>tert</i>-butyl-8-(4-chloro-benzenesulfonyl)-1<i>H</i>-pyrazolo[5,1-<i>c</i>][1,2,4]triazin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With pyridine for 4h; Heating;
  • 21
  • [ 1851-09-8 ]
  • [ 121-44-8 ]
  • [ 56413-95-7 ]
  • 5-chloro-6-[(4-chloro-benzenesulfonyl)-cyano-methyl]-pyrazine-2,3-dicarbonitrile; compound with triethyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In N,N-dimethyl-formamide at 20℃; for 1h;
  • 22
  • [ 1851-09-8 ]
  • [ 68-11-1 ]
  • 2-[(4-chlorophenyl)sulfonyl]methylidene}thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With pyridine for 10h; Heating;
  • 23
  • [ 18527-19-0 ]
  • [ 1851-09-8 ]
YieldReaction ConditionsOperation 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
  • 24
  • [ 30742-60-0 ]
  • [ 1851-09-8 ]
  • C20H18ClN3O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating;
  • 25
  • [ 1851-09-8 ]
  • [ 5499-70-7 ]
  • C24H23ClN4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating;
  • 26
  • [ 1851-09-8 ]
  • [ 326008-59-7 ]
  • C23H20ClN3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With chloro-trimethyl-silane In N,N-dimethyl-formamide Heating;
  • 27
  • [ 1851-09-8 ]
  • 2-[(4-chlorophenyl)sulfonyl]methylidene}-3-(2-oxo-2-phenylethyl)thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C
  • 28
  • [ 1851-09-8 ]
  • 3-[2-(4-chlorophenyl)-2-oxoethyl]-2-[(4-chlorophenyl)sulfonyl]methylidene}thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 90 percent / K2CO3 / dimethylformamide / 20 °C
  • 29
  • [ 1851-09-8 ]
  • 3-[2-(4-bromophenyl)-2-oxoethyl]-2-[(4-chlorophenyl)sulfonyl]methylidene}thiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 83 percent / pyridine / 10 h / Heating 2: 89 percent / K2CO3 / dimethylformamide / 20 °C
  • 30
  • [ 1851-09-8 ]
  • 7-(4-chlorophenyl)sulfonyl-2-(dimethylamino)methylidene-5-(phenylcarbonyl)pyrrolo[2,1-b]thiazol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 31
  • [ 1851-09-8 ]
  • 5-(4-bromophenyl)carbonyl-7-(4-chlorophenyl)sulfonyl-2-[(dimethylamino)methylidene]pyrrolo[2,1-b]thiazol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 32
  • [ 1851-09-8 ]
  • 5-(4-chlorophenyl)carbonyl-7-(4-chlorophenyl)sulfonyl-2-[(dimethylamino)methylidene]pyrrolo[2,1-b]thiazol-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 33
  • [ 1851-09-8 ]
  • [ 32083-31-1 ]
YieldReaction ConditionsOperation 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
  • 34
  • [ 1851-09-8 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(pyridin-3-ylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 35
  • [ 1851-09-8 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 36
  • [ 1851-09-8 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 37
  • [ 1851-09-8 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 38
  • [ 1851-09-8 ]
  • (E)-2-(4-Chloro-benzenesulfonyl)-3-cyclobutylamino-3-(3,5-dichloro-phenylamino)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 39
  • [ 1851-09-8 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-cyclobutylamino-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 40
  • [ 1851-09-8 ]
  • (E)-3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chloro-benzenesulfonyl)-3-(1,1-dimethyl-propylamino)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 41
  • [ 1851-09-8 ]
  • (E)-3-(3,5-Bis-trifluoromethyl-phenylamino)-2-(4-chloro-benzenesulfonyl)-3-propylamino-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 1851-09-8 ]
  • (E)-3-(3,5-Bis-trifluoromethyl-phenylamino)-2-(4-chloro-benzenesulfonyl)-3-(3-methyl-butylamino)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 43
  • [ 1851-09-8 ]
  • (E)-3-(3,5-Bis-trifluoromethyl-phenylamino)-2-(4-chloro-benzenesulfonyl)-3-((R)-1,2,2-trimethyl-propylamino)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 44
  • [ 1851-09-8 ]
  • (E)-3-(3,5-Bis-trifluoromethyl-phenylamino)-2-(4-chloro-benzenesulfonyl)-3-((S)-1,2,2-trimethyl-propylamino)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 45
  • [ 1851-09-8 ]
  • [ 360071-51-8 ]
YieldReaction ConditionsOperation 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
  • 46
  • [ 1851-09-8 ]
  • <i>N</i>-[5-bromo-3-(4-chloro-benzenesulfonyl)-thiophen-2-yl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 47
  • [ 1851-09-8 ]
  • <i>N</i>-[3-(4-chloro-benzenesulfonyl)-5-nitro-thiophen-2-yl]-acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 48
  • [ 1851-09-8 ]
  • [ 360071-53-0 ]
YieldReaction ConditionsOperation 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
  • 49
  • [ 1851-09-8 ]
  • <i>N</i>-[5-bromo-3-(4-chloro-benzenesulfonyl)-thiophen-2-yl]-2,2,2-trifluoro-acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 50
  • [ 1851-09-8 ]
  • <i>N</i>-[3-(4-chloro-benzenesulfonyl)-5-iodo-thiophen-2-yl]-2,2,2-trifluoro-acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 51
  • [ 1851-09-8 ]
  • <i>N</i>-[3-(4-chloro-benzenesulfonyl)-thiophen-2-yl]-2,2,3,3,4,4,4-heptafluoro-butyramide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 52
  • [ 1851-09-8 ]
  • [ 112381-94-9 ]
YieldReaction ConditionsOperation 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
  • 53
  • [ 1851-09-8 ]
  • [ 18527-41-8 ]
YieldReaction ConditionsOperation 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).
  • 54
  • [ 1851-09-8 ]
  • [ 14035-33-7 ]
  • [ 797035-86-0 ]
YieldReaction ConditionsOperation 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.
  • 55
  • [ 1851-09-8 ]
  • [ 5059-30-3 ]
  • 2-(4-chlorobenzenesulfonyl)-3-(2-chloro-1H-indol-3-yl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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
  • 56
  • [ 1196-69-6 ]
  • [ 1851-09-8 ]
  • 2-(4-chlorobenzenesulfonyl)-3-(1H-indol-5-yl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 57
  • [ 17452-27-6 ]
  • [ 1851-09-8 ]
  • [ 74-88-4 ]
  • 2-(4-Chlorophenylsulfonyl)-3-methylsulfanyl-3-(pyridin-3-ylamino)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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+).
  • 58
  • [ 1851-09-8 ]
  • [ 113504-93-1 ]
  • [ 74-88-4 ]
  • 3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation 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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