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[ CAS No. 160982-10-5 ] {[proInfo.proName]}

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Chemical Structure| 160982-10-5
Chemical Structure| 160982-10-5
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Product Details of [ 160982-10-5 ]

CAS No. :160982-10-5 MDL No. :MFCD09033309
Formula : C6H6ClNO3S2 Boiling Point : -
Linear Structure Formula :- InChI Key :ODLFFSHLXVZFPY-UHFFFAOYSA-N
M.W : 239.70 Pubchem ID :15294528
Synonyms :

Calculated chemistry of [ 160982-10-5 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.52
TPSA : 113.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.55
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : -0.38
Log Po/w (SILICOS-IT) : 1.71
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.2
Solubility : 1.5 mg/ml ; 0.00626 mol/l
Class : Soluble
Log S (Ali) : -3.14
Solubility : 0.175 mg/ml ; 0.000732 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.19
Solubility : 1.54 mg/ml ; 0.00643 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.92

Safety of [ 160982-10-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 160982-10-5 ]

* 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 [ 160982-10-5 ]

[ 160982-10-5 ] Synthesis Path-Downstream   1~19

  • 1
  • [ CAS Unavailable ]
  • [ 160982-09-2 ]
  • [ 160982-10-5 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide; sodium hydrogensulfite In water; ethyl acetate 1.2 Step 2. Step 2. 3-Acetyl-5-chloro-2-thiophenesulfonamide (3) Chlorine gas was bubbled into a stirred, 2° to 10° C. solution of 3-acetyl-5-chloro-2-(benzylthio)thiophene (2, 1 kg, 3.53 mol) in ethyl acetate (20 L) until TLC analysis indicated consumption of starting material. The solution was purged with a vigorous stream of air for 1 hour before ammonia was bubbled in, keeping the temperature between 5° and 15° C. This was continued until TLC analysis indicated consumption of the intermediate sulfenyl chloride. The mixture was again purged with air for 1 hour before water (5 L) was added and the solution was cooled to 15° C. Sodium tungstate dihydrate (0.5 eq, 1.77 mol, 583 g) was added followed by the addition of 30% hydrogen peroxide (8 L) over 5 minutes. The mixture was heated at 35° C. for 2 hours and then stirred at ambient temperature for 16 hours before water (5 L) was added and the phases were split. Water (5 L) was added to the organic phase followed by solid sodium bisulfite until a negative test for peroxide was obtained with peroxide test paper. The phases were split and the organic phase was washed first with saturated aqueous sodium bicarbonate until the pH of the wash was 8, then with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and stripped of solvent by rotary evaporation. The residual semi-solid was triturated with t-butyl methyl ether and the solid was collected by filtration, washed with t-butyl methyl ether, and dried in air to a constant weight of 597 grams (71%) of 3: mp 178°-179° C.; IR (KBr) 3340, 3260, 3089, 1682, 1553, 1508, 1403, 1360, 1224, 1153 cm-1; 1 H NMR (DMSO-d6) δ7.72 (s, 2H), 7.70 (s, 1H), 2.55 (s, 3H); Analysis for C6 H6 ClNO3 S2: Calcd: C, 30.06; H, 2.52; N, 5.84; S, 26.75. Found: C, 30.19; H, 2.51; N, 5.80; S, 26.70.
  • 2
  • [ 160982-10-5 ]
  • [ 160982-11-6 ]
YieldReaction ConditionsOperation in experiment
96.8% With N-Bromosuccinimide In ethyl acetate at 60 - 70℃; Large scale; 2 Example 2 Into a dry and clean 500L reactor, 120 kg of ethyl acetate was charged.24 kg of 3-acetyl-5-chloro-2-thiophenesulfonamide was added with stirring.The temperature was raised to 60-70 ° C; a suspension solution of 21.3 kg of N-bromosuccinimide and 85.2 kg of ethyl acetate was added dropwise, and the addition was completed in 1 to 2 hours. The thin layer monitors the reaction of the raw materials, and the solvent is concentrated and removed, and the mixture is crystallized at 0 to 10 ° C for 3 hours, and centrifuged to obtain a crude product;The crude product was added with 240 kg of deionized water, and the temperature was raised to 60-70 ° C for 1 hour. The temperature was lowered to 0 to 10 ° C for centrifugation, and the obtained wet product was dried to obtain an off-white 3-bromoacetyl-5-chloro-2-thiophenesulfonamide 28.61 kg. The molar yield was 89.8%, and the liquid phase purity was 96.8%.
72% With sulfuric acid; pyridinium hydrobromide perbromide In water; ethyl acetate 4.B Step B: Step B: 3-(2-Bromoacetyl)-5-chloro-thiophene-2-sulfonamide A 50-L, 5-necked flask equipped with a mechanical stirrer, a thermometer, and a 1 L addition funnel was charged with the product from Step A (1.087 kg, 4.55 mol) and ethyl acetate (22 L). The pale yellow suspension was cooled to 1° C. over 45 minutes using an ice-water bath and 90% pyridinium bromide perbromide (1.305 kg, 3.67 mol) was added in one portion. Sulfuric acid (544 mL) was added via the addition funnel over 10 minutes causing the temperature to rise to 5° C. The reaction mixture was stirred and, after 1 hour, TLC analysis indicated complete reaction. Thirty minutes later, water (5 L) was added and the mixture was stirred for 5 minutes before the phases were split. The organic phase was washed with saturated aqueous sodium chloride until the pH of the wash was 3 (4*5 L), dried over sodium sulfate (1 kg), filtered, and stripped of solvent by rotary evaporation. The residue was triturated with methylene chloride (2 L) and chilled for 15 minutes before the solid was collected by filtration, washed with cold methylene chloride (2 L), and dried to give the desired product (1.041 kg, 72%): mp 147°-148° C. Analysis. Calculated for C6 H5 BrClNO3 S2: C, 22.62; H, 1.58; N, 4.40; S, 20.13. Found: C, 22.66; H, 1.60; N, 4.35; S, 20.12.
72% With pyridinium hydrobromide perbromide; sulfuric acid In ethyl acetate at 1 - 5℃; for 1.5h; Large scale;
With sulfuric acid; pyridinium hydrobromide perbromide In water; ethyl acetate 1.3 Step 3. Step 3. 3-Bromoacetyl-5-chloro-2-thiophenesulfonamide (4) A 50-L, 5-necked flask equipped with a mechanical stirrer, a thermometer, and a 1-L addition funnel was charged with 3-acetyl-5-chloro-2-thiophenesulfonamide (3, 1,087 kg, 4.55 mol) and ethyl acetate (22 L). The pale yellow suspension was cooled to 1° C. over 45 minutes using an ice-water bath, and 90% pyridinium bromide perbromide (1.305 kg, 3.67 mol) was added in one portion. Sulfuric acid (544 mL) was added via the addition funnel over 10 minutes causing the temperature to rise to 5° C. The reaction mixture was stirred for 1 hour, after which TLC analysis indicated complete reaction. Thirty minutes later, water (5 L) was added and the mixture was stirred for 5 minutes before the phases were split. The organic phase was washed with saturated aqueous sodium chloride until the pH of the wash was 3 (4*5 L required), dried over sodium sulfate (1 kg), filtered, and stripped of solvent by rotary evaporation. The residue was triturated with methylene chloride (2 L) and chilled for 15 minutes before the solid was collected by filtration, washed with cold methylene chloride (2 L), and dried in air at ambient temperature to a constant weight of 1,041 kilograms (72%) of 4: mp 147°-148° C.; IR (KBr) 3381, 3263, 3093, 1694, 1532, 1403, 1336, 1163, 1102 cm-1; 1 H NMR (acetone-d6) δ7.76 (s, 1H), 7.11 (br, 2H), 4.76 (s, 2H); Analysis for C6 H5 BrClNO3 S2: Calcd: C, 22.62; H, 1.58; N, 4.40; S, 20.13. Found: C, 22.66; H, 1.60; N, 4.35; S, 20.12.

  • 3
  • [ 221910-86-7 ]
  • [ 160982-10-5 ]
YieldReaction ConditionsOperation in experiment
597 g With sodium tungstate (VI) dihydrate; dihydrogen peroxide In water at 15 - 35℃; for 19h;
  • 4
  • [ 160982-10-5 ]
  • [ 221910-84-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 5 °C / Inert atmosphere 4.2: 3.5 h / 5 - 45 °C 5.1: acetic acid; sodium hypochlorite solution / water / 0.58 h / 10 °C 5.2: 0.5 h / 20 °C / Cooling with ice
  • 5
  • [ 160982-10-5 ]
  • [ 154127-33-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide 4.1: n-butyllithium; hydroxylamine-O-sulfonic acid; sodium acetate trihydrate / hexane; tetrahydrofuran
  • 6
  • [ 160982-10-5 ]
  • [ 221910-88-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide 4.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / Inert atmosphere 4.2: 20 °C / pH 4 4.3: 15 h / 0 - 25 °C 5.1: acetonitrile / 19 h / 30 - 85 °C / Reflux
  • 7
  • 3-acetyl-5-chloro-2-thiophenesulfonamide [ No CAS ]
  • [ 138890-62-7 ]
  • 8
  • [ 160982-10-5 ]
  • [ 160982-13-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide
  • 9
  • 3-acetyl-5-chloro-2-thiophenesulfonamide [ No CAS ]
  • [ 154127-42-1 ]
  • 10
  • [ 160982-10-5 ]
  • [ 1395437-42-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide 4.1: n-butyllithium / hexane; tetrahydrofuran / 3.5 h / -70 - -66 °C / Inert atmosphere 4.2: 20 °C / pH 4 4.3: 15 h / 0 - 25 °C 5.1: acetonitrile / 19 h / 30 - 85 °C / Reflux 6.1: triethylamine / tetrahydrofuran / 2 h / -10 - -2 °C / Inert atmosphere
  • 11
  • [ 160982-10-5 ]
  • [ 160982-12-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide
  • 12
  • [ 160982-10-5 ]
  • [ 221910-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridinium hydrobromide perbromide; sulfuric acid / ethyl acetate / 1.5 h / 1 - 5 °C / Large scale 2.1: B-chlorodiisopinocampheylborane / tert-butyl methyl ether / 3.5 h / -40 - -32 °C / Inert atmosphere 2.2: 2 h / 0 - 22 °C 3.1: potassium carbonate / dimethyl sulfoxide 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 5 °C / Inert atmosphere 4.2: 3.5 h / 5 - 45 °C
  • 13
  • [ 36157-40-1 ]
  • 3-acetyl-5-chloro-2-thiophenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: thiourea / ethanol; water / 2 h / Reflux; Large scale 1.2: 3 h / Reflux; Large scale 2.1: chlorine / toluene / 0.42 h / 8 °C / Cooling with ice 3.1: ammonia / 1 h / 5 - 15 °C 4.1: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C
  • 14
  • [ 160982-09-2 ]
  • [ 160982-10-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: chlorine / toluene / 0.42 h / 8 °C / Cooling with ice 2: ammonia / 1 h / 5 - 15 °C 3: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C
  • 15
  • [ 221910-79-8 ]
  • [ 160982-10-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ammonia / 1 h / 5 - 15 °C 2: sodium tungstate (VI) dihydrate; dihydrogen peroxide / water / 19 h / 15 - 35 °C
  • 16
  • [ 165117-07-7 ]
  • [ 160982-10-5 ]
YieldReaction ConditionsOperation in experiment
91.2% With ammonia In ethyl acetate at 0 - 15℃; for 1h; 1 The above sulfonyl chloride was diluted with 105 g of ethyl acetate,Temperature control 0 ~ 15 ° C,Dropping to 420g of ammonia,The reaction was stirred until the sulfonyl chloride disappeared,Cooling to about o ° C,Stirring crystallization lh.filter,A small amount of bubble wash,The resulting solid was dried at 40 ° C,Kind of white3-acetyl-5-chloro-2-thiophenesulfonamide (162.4 g)The yield was 91.2% and the APLC purity was greater than 99%.
  • 17
  • [ 160982-10-5 ]
  • [ 1174304-97-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride; potassium iodide / dimethyl sulfoxide / 70 - 80 °C 2: toluene-4-sulfonic acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / methanol / 60 - 70 °C
  • 18
  • [ 160982-10-5 ]
  • [ 174139-72-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride; potassium iodide / dimethyl sulfoxide / 70 - 80 °C 2: toluene-4-sulfonic acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / methanol / 60 - 70 °C 3: sodium t-butanolate / tetrahydrofuran / 65 - 80 °C / Cooling with ice
  • 19
  • [ 160982-10-5 ]
  • [ 36865-41-5 ]
  • [ 1183938-55-7 ]
YieldReaction ConditionsOperation in experiment
86% With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; potassium iodide In dimethyl sulfoxide at 70 - 80℃; 1-4 Example 1 Preparation of compound III: After dissolving 100 g (0.42 mol) of compound II in 2 L dimethyl sulfoxide, pour it into a 5 L three-necked round-bottom flask, and add 115 g (0.83 mol) potassium carbonate, 10 g (0.04 mol) benzyl triethylammonium chloride and 5 g (0.03 mol) potassium iodide, then heat the three-necked round bottom flask to 70-80, and then 64 g (0.6 mol) 1-bromo-3 -Methoxypropane was slowly dropped into a three-necked round-bottom flask, and the reaction temperature was 70-80°C until the reaction was over; after the reaction, the product was transferred to a separatory funnel, and water and toluene were added to the separatory funnel for extraction. The upper toluene layer was taken, washed, dried, concentrated, and recrystallized by adding n-heptane to obtain 111.2 g of compound III with a yield of 86% and a purity of 98.8% as determined by HPLC.
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