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[ CAS No. 1851-09-8 ] {[proInfo.proName]}

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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 Pubchem ID :735829
Synonyms :

Calculated chemistry of [ 1851-09-8 ]      Expand+

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   1~101

  • 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+).
  • 59
  • [ 1851-09-8 ]
  • [ 3125-78-8 ]
  • [ 74-88-4 ]
  • 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.74 g (96%) With potassium carbonate In dichloromethane; acetone 37.1 1 1 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-methylsulfanyl-2-propenenitrile A solution of 4-chlorophenylsulfonylacetonitrile (1.0 g, 4.64 mmol) in dry acetone (10 ml) was stirred while dry potassium carbonate (1.28 g, 9.28 mmol) and 3-cyanophenyl isothiocyanate (0.78 g, 4.87 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 (0.859 ml, 13.9 mmol) was added to the filtrate, and stirring was continued for 3 h. 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 1.74 g (96%) of the title compound as golden brown crystals. Mp 168-170° C. 1H NMR (200 MHz, CDCl3): δ=2.22 (s, 3H), 7.50-7.68 (m, 6H), 7.84-7.93(m, 2H), 9.89 (br s, 1H).
  • 60
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 74-88-4 ]
  • 3-[N-(3,5-Bis(trifluoromethyl)phenyl)-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.52 g (20%) With potassium carbonate In acetone 11.1 1 1 3-[N-(3,5-Bis(trifluoromethyl)phenyl)-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile To a solution of 4-chlorophenylsulfonylacetonitrile (1.10 g, 5.1 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, 5.3 mmol) were added. The resulting mixture was stirred at room temperature under nitrogen. After 2 h methyl iodide (3.86 ml, 61.2 mmol) was added. The mixture was stirred at room temperature for 18 h, followed by filtration and concentration. Crystallisation from ethyl acetate/heptane 1:3 gave 0.52 g (20%) of the title compound. 1H NMR (300 MHz, CDCl3): δ=2.40 (s, 3H), 3.65 (s, 3H), 7.36 (s, 2H), 7.42 (d, 2H), 7.58 (s, 1H), 7.65 (d, 2H);); El SP/MS: 514 (M+).
  • 61
  • [ 1851-09-8 ]
  • [ 590-17-0 ]
  • 2-(4-chlorophenylsulfonyl)succinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate 4 Preparation of 2-(4-chlorophenylsulfonyl)succinonitrile EXAMPLE 4 Preparation of 2-(4-chlorophenylsulfonyl)succinonitrile To a 500 mL reaction flask was added 2.0 g (51.0 mmole) sodium hydride (60% dispersion in oil) and 20 mL hexanes. The hexanes were removed by pipette and replaced by 90 mL dry tetrahydrofuran (THF). The suspension was cooled to 0° C. and a solution of 10.0 g (46.4 mmole) 4-chlorophenylsulfonyl acetonitrile in 90 mL THF was added via addition funnel over 10 minutes maintaining the reaction temperature below 12° C. The resulting solution was removed from the cold bath and stirred at room temperature for 40 min. The solution was recooled to 0°C. and 3.4 mL (48.7 mmole) bromoacetonitrile in 5 mL THF was added dropwise via addition funnel. After 5 minutes, the reaction was removed from the cold bath and stirred at room temperature for two hours. The reaction was quenched with 1 mL of saturated ammonium chloride and concentrated to an oil which was transferred with 150 mL of dichloromethane to a separatory funnel containing 120 mL water. The organic layer was separated and washed once more with 120 mL water and once with 120 mL brine. The organic layer was then dried (Na2 SO4), filtered, concentrated, and chromatographed through a bed of silica gel using 85:15 hexane:ethyl acetate. Isolation gave 1.4 g (12% yield) of the title compound as a yellow powder that was 96% pure by HPLC, m.p. 130-137° C.
  • 62
  • [ 107-85-7 ]
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 21908-53-2 ]
  • 3-[3,5-bis(trifluoromethyl)phenylamino]-3-(3-methylbutylamino)-2-(4-chlorophenylsulfonyl)-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
317 mg (12%) With hydrogenchloride; magnesium sulfate; triethylamine In ice-water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile 6 Synthesis of 3-[3,5-bis(trifluoromethyl)phenylamino]-3-(3-methylbutylamino)-2-(4-chlorophenylsulfonyl)-2-propenenitrile Example 6 Synthesis of 3-[3,5-bis(trifluoromethyl)phenylamino]-3-(3-methylbutylamino)-2-(4-chlorophenylsulfonyl)-2-propenenitrile To a solution of 3,5-bis(trifluoromethyl)phenylisothiocyanate (1,44 g, 5.31 mmol) in DCM (15 mL) and acetonitrile (5 mL) first 4-chlorophenylsulfonylacetonitrile (1.10 g, 5.10 mmol) and then triethylamine (1.0 mL) were added. The resulting mixture was stirred at room temperature for 2 h 15 min, and then isoamylamine (0.65 mL, 5.59 mmol), mercury(II) oxide (2.70 g, 12.47 mmol) and magnesium sulfate (0.8 g) were added. Stirring was continued for 2 d. The mixture was then filtered, poured into a mixture of ice-water (200 mL) and concentrated hydrochloric acid (2 mL), phases were separated, the aqueous layer was extracted twice with DCM (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated. Column chromatography of the residue (100 g silica gel, gradient elution with heptane/ethyl acetate 10:0 to 3:1) gave 317 mg (12%) of the title compound as an oil. 1 H NMR (300 MHz, DMSO-d6): δ=0.79 (d, J=7 Hz, 6H), 1.39 (q, J=7 Hz, 2H), 1.50 (nonett, J=7 Hz, 1H), 3.31 (m, 2H), 7.27 (s, 2H), 7.67-7.80 (m, 5H), 8.13 (s, br, 1H), 9.76 (s, 1H); LCMS: elution at 16.23 min, MH+: 540.
317 mg (12%) With hydrogenchloride; magnesium sulfate; triethylamine In ice-water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile 6 Example 6. Example 6. Synthesis of 3-[3,5-bis(trifluoromethyl)phenylamino]-3-(3-methylbutylamino)-2-(4-chlorophenylsulfonyl)-2-propenenitrile To a solution of 3,5-bis(trifluoromethyl)phenylisothiocyanate (1,44 g, 5.31 mmol) in DCM (15 mL) and acetonitrile (5 mL) first 4-chlorophenylsulfonylacetonitrile (1.10 g, 5.10 mmol) and then triethylamine (1.0 mL) were added. The resulting mixture was stirred at room temperature for 2 h 15 min, and then isoamylamine (0.65 mL, 5.59 mmol), mercury(II) oxide (2.70 g, 12.47 mmol) and magnesium sulfate (0.8 g) were added. Stirring was continued for 2 d. The mixture was then filtered, poured into a mixture of ice-water (200 mL) and concentrated hydrochloric acid (2 mL), phases were separated, the aqueous layer was extracted twice with DCM (20 mL) and the combined extracts were dried (magnesium sulfate) and concentrated. Column chromatography of the residue (100 g silica gel, gradient elution with heptane/ethyl acetate 10:0 to 3:1) gave 317 mg (12%) of the title compound as an oil. 1H NMR (300 MHz, DMSO-d6): δ = 0.79 (d, J = 7 Hz, 6H), 1.39 (q, J = 7 Hz, 2H), 1.50 (nonett, J = 7 Hz, 1H), 3.31 (m, 2H), 7.27 (s, 2H), 7.67-7.80 (m, 5H), 8.13 (s, br, 1H), 9.76 (s, 1H); LCMS: elution at 16.23 min, MH+: 540.
  • 63
  • [ 78-88-6 ]
  • [ 1851-09-8 ]
  • 1-(p-chlorophenylsulfonyl)-1-cyano-2,2-bis(thio-2'-chloroallyl)ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With carbon disulfide; potassium hydroxide In 1,4-dioxane; <i>N</i>-methyl-acetamide; ethyl acetate 4 Preparation of 1-(p-chlorophenylsulfonyl)-1-cyano-2,2-bis(thio-2'-chloroallyl)ethylene EXAMPLE 4 Preparation of 1-(p-chlorophenylsulfonyl)-1-cyano-2,2-bis(thio-2'-chloroallyl)ethylene To a suspension of 9.9 gm of pulverized potassium hydroxide in 120 ml of dioxane was added 16.17 gm of p-chlorophenylsulfonyl-cyanomethane over 1 hour. Afterwards, 12 ml of carbon disulfide was added. The system was stirred at room temperature for 18 hours and then the system was diluted with 200 ml of ether. The resulting precipitate was filtered and washed with ether. The product was then suspended in 120 ml of dimethylformamide. 25.52 gm of 2,3-dichloropropene was slowly added to the system at from 0° to 10° C. The system was stirred at 20° C. for 20 hours and the solution then poured into water. The product was extracted with methylene chloride. The product was separated and purified by silica gel column chromatography using ethyl acetate as the elutant. The product was isolated and the solvent removed to give the 1-(p-chlorophenylsulfonyl)-1-cyano-2,2-bis(thio-2'-chloroallyl)ethylene as a brown oil. Listed as Compound No. 20 in Table III.
  • 64
  • [ 1851-09-8 ]
  • [ 5470-11-1 ]
  • [ 497-19-8 ]
  • [ 70661-64-2 ]
YieldReaction ConditionsOperation in experiment
70% In ethanol; water 1 2-(4-Chlorophenylsulfonyl)-N-Hydroxyethanimidamide EXAMPLE 1 2-(4-Chlorophenylsulfonyl)-N-Hydroxyethanimidamide 50 g. (0.23 mole) of 4-chlorophenylsulfonylacetonitrile were dissolved in 1.5 liters of ethanol and 16 g. (0.23 mole) of hydroxylamine HCl in 150 ml. of water was added to this solution, followed by the addition of 14.4 g. (0.12 mole) of Na2 CO3 in 150 ml. of water. This reaction mixture was stirred at room temperature overnight. 58 g. crude product were filtered off; this was recrystallized from about 2.5 liters of ethanol to give 40 g. of the product (70% yield). Analysis for: C8 H9 ClN2 O3 S-- Calculated: C, 38.65; H, 3.65; N, 11.27; Cl, 14.26; S, 12.90, Found: C, 38.53; H, 3.65; N, 11.28; Cl, 14.22; S, 12.63.
  • 65
  • [ 1851-09-8 ]
  • [ 5059-30-3 ]
  • 2-(4-Chloro-benzenesulfonyl)-3-(2-chloro-1H-indol-3-yl)-acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% In ethanol for 12h; Heating / reflux; A.1.A To a solution of the appropriate carbonylcompound (1 mmole) in ethanol 4 ml, the appropriate activated methylencompound (1 mmole) and a catalytic amount of piperidine (0.1 mmole) was added. The reaction mixture was heated at reflux for 12 hours. The products were isolated either by, Step A: cooling filtration and crystallisation or Step B: Evaporation of solvent followed by column chromatography; The title compound was prepared from 2-chloro-3-formyl-indole 4-chlorophenylsulfonylacetonitrile in 35% yield. 1H NMR (DMSO-d6): δ ppm 7.31 (m, 2 H), 7.49 (d, J=7.16 Hz, 1 H), 7.81 (d, 2 H), 8.02 (d, J=4.90 Hz, 2 H), 8.15 (d, J=7.54 Hz, 1 H), 8.32 (s, 1 H), 13.89 (s, 1 H); HPLC-MS (Method A): m/z=378 (M+1); Rt=4.37 min.
  • 66
  • [ 1851-09-8 ]
  • [ 1620-98-0 ]
  • (E)-2-(4-Chloro-Benzenesulfonyl)-3-(3,5-Di-Tert-Butyl-4-Hydroxy-Phenyl)-Acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% 85.A (E)-2-(4-Chloro-Benzenesulfonyl)-3-(3,5-Di-Tert-Butyl-4-Hydroxy-Phenyl)-Acrylonitrile Step A: The title compound was prepared from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and 4-chlorophenylsulfonylacetonitrile in 72% yield 1H NMR (CDCl3): δ 1.45 (s, 18 H) 6.01 (s, 1 H) 7.56 (d, J=8.59 Hz, 2 H) 7.83 (s, 2 H) 7.94 (d, J=8.59 Hz, 2 H) 8.12 (s, 1 H); HPLC-MS (Method A): m/z=432 (M+1); Rt=4.88 min.
  • 67
  • [ 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
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;
  • 68
  • [ 1851-09-8 ]
  • [ 113504-93-1 ]
  • [ 74-88-4 ]
  • [ 268207-26-7 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 5-isothiocyanato-benzo[1,3]dioxole With potassium carbonate In acetone at 20℃; for 4h; Stage #2: methyl iodide In acetone at 20℃; for 0.833333h;
  • 69
  • [ 1851-09-8 ]
  • [ 3125-78-8 ]
  • [ 74-88-4 ]
  • [ 268207-36-9 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3-cyanophenyl isothiocyanate With potassium carbonate In acetone at 20℃; for 20h; Stage #2: methyl iodide In acetone at 20℃; for 3h;
  • 70
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 74-88-4 ]
  • [ 268207-23-4 ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3,5-bistrifluoromethylphenylisothiocyanate With potassium carbonate In acetone at 20℃; for 1h; Stage #2: methyl iodide With sodium hydrogencarbonate In water; acetone at 20℃; for 3.5h;
  • 71
  • [ 1851-09-8 ]
  • [ 23165-29-9 ]
  • [ 74-88-4 ]
  • 3-[N-(3,5-bis(trifluoromethyl)phenylamino)-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
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;
  • 72
  • [ 1851-09-8 ]
  • [ 6590-93-8 ]
  • [ 74-88-4 ]
  • [ 268207-25-6 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 3,5-dichlorophenylisothiocyanate With potassium carbonate In acetone at 20℃; for 4h; Stage #2: methyl iodide In acetone at 20℃; for 0.75h;
  • 73
  • [ 1851-09-8 ]
  • [ 104968-58-3 ]
  • [ 74-88-4 ]
  • [ 268207-28-9 ]
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;
  • 74
  • [ 75-15-0 ]
  • [ 1851-09-8 ]
  • [ 74-88-4 ]
  • [ 124392-37-6 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: carbon disulfide; 2-(4-chlorobenzenesulfonyl)acetonitrile With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 1h; Stage #2: methyl iodide In dimethyl sulfoxide at 0 - 20℃; for 18h; To a solution of 2-(4-chlorobenzenesulfonyl) acetonitrile (600 mg, 2.78 mmol) in anhydrous DMSO (8 ml) under an argon atmosphere was added carbon disulfide (212 mg, 2.78 mmol). The reaction mixture was cooled to approximately 0° C. and 2 equivalents of sodium hydride (5.56 mmol) was added in one portion. The resulting thick reaction mixture was swirled until homogeneous and allowed to warm to room temperature for one hour with stirring. The reaction mixture was cooled again to 0° C. and 2 equivalents of iodomethane (5.56 mmol) was added under argon. The reaction mixture was allowed to gradually warm to room temperature and after 18 hours deionized water was added (30 ml) and the resulting slurry was stirred for 15 minutes. The solid was collected by filtration, washed with deionized water, and dried. The crude solid product thus obtained was dissolved in 25% hexanes/chloroform and purified via flash chromatography. The resulting solution was concentrated in vacuo to provide the titled compound as a light yellow solid in 65% yield. 1H NMR (300 MHz, CDCl3): δ8.0-7.9 (d, 2H), 7.6-7.5 (d, 2H), 2.7 (s, 3H), 2.6 (s, 3H).
65% Stage #1: carbon disulfide; 2-(4-chlorobenzenesulfonyl)acetonitrile With sodium hydride In dimethyl sulfoxide at 0 - 20℃; Inert atmosphere; Stage #2: methyl iodide In dimethyl sulfoxide at 0 - 20℃; for 18h; Inert atmosphere; 4.3 Syntheses of intermediates and final compounds (0021) 2-(4-Chlorobenzenesulfonyl)-3,3-bis-methylsulfanyl-acrylonitrile (4, 4-chlorobenzenesulfonyl-). To a solution of 2-(4-chlorobenzenesulfonyl)acetonitrile (600mg, 2.78mmol) in anhydrous DMSO (8ml) under an argon atmosphere was added carbon disulfide (212mg, 2.78mmol). The reaction mixture was cooled to approximately 0°C and 2equiv of sodium hydride (5.56mmol) were added in one portion. The resulting thick reaction mixture was swirled until homogeneous and allowed to warm to room temperature for one hour with stirring. The reaction mixture was cooled again to 0°C and 2equiv of iodomethane (5.56mmol) were added under argon. The reaction mixture was allowed to gradually warm to room temperature and deionized water was added (30ml) after 18h of stirring. The resulting slurry was stirred for another 15min. The solid was collected by filtration, washed with deionized water, and dried. The crude solid product thus obtained was dissolved in 25% hexanes/chloroform and purified via flash chromatography to yield the titled compound as a light yellow solid in 65% yield. lH NMR (300MHz, CDCl3): δ 8.0-7.9 (d, 2H), 7.6-7.5 (d, 2H), 2.7 (s, 3H), 2.6 (s, 3H).
  • 75
  • [ 1851-09-8 ]
  • [ 3296-02-4 ]
  • [ 1189052-41-2 ]
YieldReaction ConditionsOperation in experiment
71% With sodium methylate In methanol at 20℃;
  • 76
  • [ 1851-09-8 ]
  • [ 622-37-7 ]
  • [ 1189052-40-1 ]
YieldReaction ConditionsOperation in experiment
54% With sodium methylate In methanol at 20℃;
  • 77
  • [ 107-14-2 ]
  • [ 98-60-2 ]
  • [ 1851-09-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-chlorobenzenesulfonyl chloride With water; zinc Stage #2: chloroacetonitrile In isopropyl alcohol
Stage #1: 4-chlorobenzenesulfonyl chloride With sodium hydrogencarbonate; sodium sulfite In water at 100℃; for 0.5h; Microwave irradiation; Stage #2: chloroacetonitrile In water at 100℃; for 0.333333h; Microwave irradiation;
  • 78
  • [ 1851-09-8 ]
  • methyl 2-azido-4,5-dimethoxybenzoate [ No CAS ]
  • [ 1227262-52-3 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 20℃;
  • 80
  • [ 1851-09-8 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 36603-45-9 ]
YieldReaction ConditionsOperation in experiment
98% With [2,2]bipyridinyl; palladium(II) trifluoroacetate; water; trifluoroacetic acid In tetrahydrofuran at 80℃; for 36h; Inert atmosphere; Schlenk technique;
  • 81
  • [ 83-72-7 ]
  • [ 1851-09-8 ]
  • [ 87-48-9 ]
  • C26H14BrClN2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(II) ferrite In water for 0.5h; Reflux; Green chemistry;
  • 82
  • [ 83-72-7 ]
  • [ 611-09-6 ]
  • [ 1851-09-8 ]
  • C26H14ClN3O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With copper(II) ferrite In water for 0.5h; Reflux; Green chemistry;
  • 83
  • [ 1851-09-8 ]
  • [ 5472-84-4 ]
  • [ 87-48-9 ]
  • C29H16BrClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(II) ferrite In water for 0.5h; Reflux; Green chemistry;
  • 84
  • [ 1851-09-8 ]
  • [ 5472-84-4 ]
  • [ 91-56-5 ]
  • C29H17ClN2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With copper(II) ferrite In water for 0.5h; Reflux; Green chemistry;
  • 85
  • [ 83-72-7 ]
  • [ 1851-09-8 ]
  • [ 91-56-5 ]
  • C26H15ClN2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With copper(II) ferrite In water for 0.5h; Reflux; Green chemistry;
  • 86
  • [ 1851-09-8 ]
  • 4-chloro-6-(cyclohex-1-en-1-yl)pyrimidin-5-amine [ No CAS ]
  • 7-[(4-chlorobenzene)sulfonyl]-4-(cyclohex-1-en-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile With sodium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane at 0 - 25℃; for 0.416667h; Inert atmosphere; Stage #2: 4-chloro-6-(cyclohex-1-en-1-yl)pyrimidin-5-amine With palladium diacetate; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In tetrahydrofuran; 1,4-dioxane at 130℃; for 5h; Microwave irradiation; Inert atmosphere; 21 Example i: 7- [(4-ebjorobenzene)sulfonyl]-4-(cyclohex-i-en-i-yI)- 5H-pyrrolo [3 ,2-d]pyrimidin-6-amine Example i: 7- [(4-ebjorobenzene)sulfonyl]-4-(cyclohex-i-en-i-yI)- 5H-pyrrolo [3 ,2-d]pyrimidin-6-amine To a stirred and nitrogen degassed solution of 2-(4-chlorobenzenesulfonyl)acetonitrile (CM 1851-09-8; 123 mg, 572 iimol) in anhydrous dioxane (0.5 mL) was added sodiobis(trimethylsilyl)amine [i M in THF] (668 jiL, 668 jimol) at o Ge. The mixture was stirred at o “C for 20 mm and then at it for mm. This mixture was added to a previously nitrogen degassed solution 4-4-chloro-6-(cyelohex-1-en-1-yl)pyrimidin-5- amine (Intermediate 100 mg, 477 pmol), (acetyloxy)palladio acetate (4.28 mg, 19 imol) and 2,8,9-tns(2-methylpropyl)-2,5, 8,9-tetraaza-1- phosphabicyclo[3.3.3jundecane (14 ilL, 38 pmol) in anhydrous dioxane (0.5 mL). The reaction mixture was heated under microwave irradiation at 130 “C for 5 h. The reaction mixture was diluted with 0.2 M aq. NaOH solution and washed with MTBE. The separated aqueous phase was neutralised with io% aq. citric acid solution, extracted with EtOAc:2-methylox&ane (2:1) and dried (H-frit). The organic phase was concentrated in vacuo. The crude product was purified by column chromatography (basic silica, 50-100% EtOAc / petroleum ether, and then with o-io% MeOH (with o.i% formic acid) I EtOAc). The residue was triturated with MTBE and then purified by column chromatography (preparaLive-HPLC, 20-60% acetonitrile / water (with o.i% ammonia)) to afford the title compound.1H NMR (400 MHz, DMSO-d6) 6 ppm i.g - 1.78 (m, 4 H) 2.21 - 2.32 (m, 2 H) 2.41 -2.52 (m, 2 H) 6.44 (br. a, 1 H) 6.82 (s, 2 H) 7.64 (d, J=8 Hz, 2 H) 8.05 (d, J=8 Hz, 2 H)8.54 (s, t H) 10.91 (hr. s., 1 H).MS E’: 389
  • 87
  • [ 4858-85-9 ]
  • [ 1851-09-8 ]
  • 2-(4-chlorobenzenesulfonyl)-2-(3-chloropyrazin-2-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 100℃; for 0.5h; Microwave irradiation; 3 Intermediate 3 2-(4-chlorobenzenesulfonyl)-2-(3-chloropyrazin-2-yl)acetonitrile To a stirred solution of 2,3-dichloropyrazine (CAS 4858-85-9; 156 μ., 1.50 mmol) and 2-(4-chlorophenylsulfonyl)acetonitrile (CAS 1851-09-8; 323 mg, 1.50 mmol) in DMF (1 mL) was added DBU (452 μ,, 3.00 mmol). The reaction was heated in a microwave at 100 °C for 30 min. The reaction mixture was diluted with ammonium chloride solution, extracted with EtOAc / tetrahydrofuran (2:1), the combined organics dried (H frit) and evaporated to dryness. The crude product was purified by column chromatography silica (silica, 0-100% EtOAc / petroleum ether) to afford the title compound. MS ES+: 328
  • 88
  • (S)-methyl 2-{(R)-4-[(tert-butoxycarbonyl)-amino]-3-oxoisothiazolidin-2-yl}-3-methylbutanoate [ No CAS ]
  • [ 1851-09-8 ]
  • (2S)-methyl 2-((2R)-2-((tert-butoxycarbonyl)amino)-3-((((4-chlorophenyl)sulfonyl)(cyano)methyl)thio)propanamido)-3-methylbutanoate [ No CAS ]
  • (2S,5R,11R,14S)-dimethyl 5,11-bis((tert-butoxycarbonyl)amino)-8-((4-chlorophenyl)sulfonyl)-8-cyano-2,14-diisopropyl-4,12-dioxo-7,9-dithia-3,13-diazapentadecane-1,15-dioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 78% 2: 15% In methanol at 24℃; 15 4.2. General procedure for synthesis of adducts 2a-2i and 3a-3i General procedure: To a stirred solution of the sulfenyl amide peptide 1 (20 mg,0.060 mmol) in 3 mL of 3:1 methanol:HEPES buffer (HEPES,50 mM, NaCl, 100 mM, EDTA, 1 M, pH 7.0) was added the sulfone-containing nucleophile (1.1 equiv) and the mixture stirred at room temperature (24 C). When the reaction was judged completeby TLC analysis, methanol was completely removed by blowinga stream of nitrogen gas on the solution, and the resulting aqueous solution extracted with ethyl acetate or dichloromethane(2 2 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The products were isolated by column chromatography on silica gel eluted with mixtures of either ethyl acetate-hexane or methanol-dichloromethane. (2S)-Methyl 2-((2R)-2-((tert-butoxycarbonyl)amino)-3-((((4-chlorophenyl)sulfonyl)(cyano)methyl)thio)propanamido)-3-methylbutanoate (2i) Colorless oil (5 mg, 15%) Rf = 0.30 (20% ethyl acetate/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.03 (d, J = 9.0 Hz, 1H), δ 7.95 (d, J = 8.5 Hz, 1H), δ 7.61-7.64 (m, 2H), δ 6.99 (d, J = 7.5 Hz, 0.5H), δ 6.86 (d, J = 8.0 Hz, 0.5H), δ 5.46-5.57 (m, 2H), δ 4.47-4.54 (m, 2H), δ 3.76 (s, 2H), δ 3.75 (s, 1H), δ 3.54 (dd, J = 14.5, 4.0 Hz, 0.5H), δ 3.13-3.26 (m, 1.5H), δ 2.17-2.27 (m, 1H), δ 1.48 (s, 4H), δ 1.47 (s, 5H), δ 0.91-0.99 (m, 6H); 13C NMR (CDCl-3, 125 MHz) δ 171.7, 171.6, 170.0, 169.8, 155.6, 155.5, 142.8, 142.7, 132.9, 132.8, 131.7, 131.6, 130.0, 129.9, 112.0, 111.8, 81.3, 81.0, 57.7, 57.6, 57.4, 56.8, 54.1, 53.5, 52.4, 52.3, 36.1, 35.6, 31.0, 30.8, 28.3, 28.2, 19.0, 18.9, 17.6, 17.5; IR (cm-1) 3416, 3032, 2982, 2945, 2862, 2304, 1741, 1662, 1581, 1372, 1351, 1260, 1152, 1069, 823, 734, 708; HRMS (ESI-TOF, [M+Na]+) m/z calculated for C22H30ClN3O7S2: 570.1111, found 570.1104.
  • 89
  • [ 1851-09-8 ]
  • 2-(azetidin-1-yl)benzaldehyde [ No CAS ]
  • C18H15ClN2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In ethanol at 20℃; for 0.5h;
  • 90
  • [ 1851-09-8 ]
  • [ 1840-19-3 ]
  • [ 74-88-4 ]
  • C17H12ClF3N2O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; 1-isothiocyanato-3-trifluoromethyl-benzene With potassium carbonate In acetone at 25℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In acetone at 25℃; for 2h; Inert atmosphere;
  • 91
  • [ 1851-09-8 ]
  • [ 103-72-0 ]
  • [ 74-88-4 ]
  • C16H13ClN2O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(4-chlorobenzenesulfonyl)acetonitrile; phenyl isothiocyanate With potassium carbonate In acetone at 25℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In acetone at 25℃; for 2h; Inert atmosphere;
  • 92
  • [ 1851-09-8 ]
  • [ 66569-06-0 ]
  • C21H14Cl2N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; N,N-dimethylethylenediamine; copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 19h; Inert atmosphere; Schlenk technique; 10 Example 10: At room temperature,The corresponding 2-bromo-N-phenylbenzenesulfonamide compound (0.2 mmol), 4-chlorobenzenesulfonylacetonitrile (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with nitrogen and equipped with a magnetic stirrer. 0.2 mmol), cuprous chloride (0.02 mmol), N,N'-dimethylethylenediamine (0.06 mmol), sodium carbonate (0.4 mmol) under nitrogen, 2.0 mL DMF was added by syringe, and the reaction tube was placed. Stir in a 110 ° C oil bath for 19 hours. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (7:1, v/v)).The target product was obtained 39.1 mg,Yield 46%
  • 93
  • [ 1851-09-8 ]
  • 2-bromo-N-(4-bromophenyl)benzamide [ No CAS ]
  • C21H14BrClN2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With copper(l) iodide; N,N-dimethylethylenediamine; barium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 17h; Inert atmosphere; Schlenk technique; 14 Example 14 At room temperature,The corresponding 2-bromo-N-phenylbenzenesulfonamide compound (0.2 mmol) was sequentially added to a 25 ml Schlenk tube filled with nitrogen and equipped with a magnetic stirrer.4-chlorobenzenesulfonylacetonitrile (0.3 mmol),Cuprous iodide (0.04 mmol),N,N'-dimethylethylenediamine (0.12 mmol),2.0 mL of NMP was added to the syringe with cesium carbonate (0.8 mmol) under nitrogen.The reaction tube was placed in a 120 ° C oil bath for 17 hours. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v/v)).The target product was obtained 38.2 mg,The yield is 39%.
  • 94
  • [ 1851-09-8 ]
  • [ 55204-50-7 ]
  • C22H17ClN2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere; Schlenk technique; 18 Example 18: At room temperature,The corresponding 2-bromo-N-phenylbenzenesulfonamide compound (0.2 mmol), 4-chlorobenzenesulfonylacetonitrile (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with nitrogen and equipped with a magnetic stirrer. 0.4 mmol), cuprous iodide (0.04 mmol), N,N'-dimethylethylenediamine (0.04 mmol), potassium carbonate (0.6 mmol) under nitrogen, 2.0 mL of DMSO was added by syringe, and the reaction tube was placed. Stir in a 100 ° C oil bath for 15 hours. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v/v)).The target product was obtained 53.8 mg,The yield is 61%.
  • 95
  • [ 1851-09-8 ]
  • [ 10282-57-2 ]
  • C21H15ClN2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With potassium carbonate; N,N-dimethylethylenediamine; copper(I) bromide In 1-methyl-pyrrolidin-2-one at 110℃; for 12h; Inert atmosphere; Schlenk technique; 3 Example 3: The corresponding 2-bromo-N-phenylbenzenesulfonamide compound (0.2 mmol) was added to a 25 ml Schlenk tube filled with nitrogen and equipped with a magnetic stirrer at room temperature, 4-chlorobenzenesulfonate. Acyl acetonitrile (0.4 mmol), cuprous bromide (0.05 mmol), N,N'-dimethylethylenediamine (0.06 mmol), potassium carbonate (0.7 mmol) under nitrogen, 2.0 mL of NMP was added by syringe, and the reaction was carried out. The tube was placed in a 110 ° C oil bath for 12 hours. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v/v)).The target product was obtained 64.5 mg,The yield was 70%.
  • 96
  • [ 1851-09-8 ]
  • (E)-3-(3-chlorobenzylidene)-1-methylpiperidin-4-one [ No CAS ]
  • [ 1122-91-4 ]
  • (E)-4-(4-bromophenyl)-8-(3-chlorobenzylidene)-3-((4-chlorophenyl)sulfonyl)-6-methyl-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With piperidine In ethanol at 20℃; for 18h; Green chemistry;
  • 97
  • [ 1851-09-8 ]
  • (E)-1-methyl-3-(naphthalen-2-ylmethylene)piperidin-4-one [ No CAS ]
  • [ 1122-91-4 ]
  • (E)-4-(4-bromophenyl)-3-((4-chlorophenyl)sulfonyl)-6-methyl-8-(naphthalen-2-ylmethylene)-5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With piperidine In ethanol at 20℃; for 18h; Green chemistry;
  • 98
  • [ 637-87-6 ]
  • [ 1624363-23-0 ]
  • [ 1851-09-8 ]
YieldReaction ConditionsOperation in experiment
61% With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In acetonitrile at 20℃; for 24h; Inert atmosphere; UV-irradiation;
  • 99
  • [ 1851-09-8 ]
  • [ 55738-12-0 ]
  • 2-(1-benzyl-4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene)-2-((4-chlorophenyl)sulfonyl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With 4-(Methylthio)benzaldehyde In N,N-dimethyl-formamide at 100℃; for 5h; General procedure for the preparation of compounds 4a-n General procedure: A solution of imidazole N-oxide 1 (1 mmol), nitrile 3 (1 mmol) and 2 (1 mmol) in 4ml of DMF was stirred at 100°C for 5 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel(eluent: 100% ethyl acetate) to give the corresponding product 4.
  • 100
  • [ 1851-09-8 ]
  • [ 63455-73-2 ]
  • 2-((4-chlorophenyl)sulfonyl)-2-(1,4,5-trimethyl-1,3-dihydro-2H-imidazol-2-ylidene)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With 4-(Methylthio)benzaldehyde In N,N-dimethyl-formamide at 100℃; for 5h; General procedure for the preparation of compounds 4a-n General procedure: A solution of imidazole N-oxide 1 (1 mmol), nitrile 3 (1 mmol) and 2 (1 mmol) in 4ml of DMF was stirred at 100°C for 5 h. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel(eluent: 100% ethyl acetate) to give the corresponding product 4.
  • 101
  • [ 1624363-23-0 ]
  • [ 673-41-6 ]
  • [ 1851-09-8 ]
YieldReaction ConditionsOperation in experiment
With sodium metabisulfite In 1,2-dichloro-ethane at 20℃; Inert atmosphere; 4 Example 4 At room temperature, add 4-chlorophenyl diazonium salt (0.2 mmol), sodium metabisulfite (0.4 mmol), 3-azido-2-methylbut-3-ene-2-into the dry reaction tube in sequence Alcohol (0.3mmol), plug the reaction tube with a stopper and replace it with high-purity nitrogen or argon three times to make the system under anaerobic conditions, then add 1,2-dichloroethane (2mL), and stir at room temperature Until TLC monitors the complete reaction. The reaction solution was directly concentrated under reduced pressure, and the mixed system of petroleum ether and ethyl acetate was used as the mobile phase for column chromatography to separate the corresponding sulfonyl acetonitrile compound Example 4.
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