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[ CAS No. 96-72-0 ] {[proInfo.proName]}

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Chemical Structure| 96-72-0
Chemical Structure| 96-72-0
Structure of 96-72-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 96-72-0 ]

CAS No. :96-72-0 MDL No. :MFCD00035780
Formula : C6H5ClN2O4S Boiling Point : -
Linear Structure Formula :- InChI Key :ZAJALNCZCSSGJC-UHFFFAOYSA-N
M.W : 236.63 Pubchem ID :66784
Synonyms :

Calculated chemistry of [ 96-72-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.27
TPSA : 114.36 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) : -7.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.09
Log Po/w (XLOGP3) : 0.94
Log Po/w (WLOGP) : 1.98
Log Po/w (MLOGP) : -0.12
Log Po/w (SILICOS-IT) : -1.41
Consensus Log Po/w : 0.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.95 mg/ml ; 0.00823 mol/l
Class : Soluble
Log S (Ali) : -2.93
Solubility : 0.279 mg/ml ; 0.00118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.97
Solubility : 2.55 mg/ml ; 0.0108 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 96-72-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280 UN#:N/A
Hazard Statements:H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 96-72-0 ]

* 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.

  • Upstream synthesis route of [ 96-72-0 ]
  • Downstream synthetic route of [ 96-72-0 ]

[ 96-72-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 100-00-5 ]
  • [ 96-72-0 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: at 120℃;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; Cooling with ice
9.45 g 1-Chloro-4-nitrobenzene (60 mmol) was heated in 20 ml chlorosulfonic acid at 120° C. overnight. The mixture was then poured onto 400 g ice and it was extracted four times with 50-50 ml dichloromethane. The combined organic layer was washed twice with brine, dried over MgSO4. Then it was added dropwise to an ice cold solution of 50 ml tetrahydrofurane and 40 ml of 25percent NH4OH solution. After the addition it was stirred for an additional hour at room temperature. Then it was evaporated under reduced pressure, 200 ml water, 10 ml concentrated hydrochloric acid solution were added carefully and was extracted three times with 100-100 ml ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4 and evaporated off again. Product was filtered from diethyl ether as a brown solid. Yield: 6.53 g (46percent). Ret. time: 2.55 min., (M+H)=235.
Reference: [1] Patent: US2014/57911, 2014, A1, . Location in patent: Paragraph 0389; 0390
[2] Patent: US2011/152246, 2011, A1,
[3] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 18 - 26
[4] Patent: WO2013/156861, 2013, A2,
[5] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
[6] Patent: WO2007/150001, 2007, A1,
  • 2
  • [ 4533-95-3 ]
  • [ 96-72-0 ]
YieldReaction ConditionsOperation in experiment
90% With ammonia In water at 10 - 20℃; To 28percent ammonia water (4.71 g, 69.2 mmol), compound 3 (4.43 g, 17.3 mmol) was added in small portions at 10 °C. When the addition was complete, the reaction was stirred at room temperature overnight. The suspension was acidified with 5 mol/L hydrochloric acid to pH 7. The white precipitate was collected by filtration to give benzenesulfonamide 4, 3.68 g, yield 90percent, m.p. 184-185 °C 1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.969 (d, 1H, JH = 8.8 Hz, Ar-H), 8.017 (s, 2H, SO2NH2), 8.414-8.442 (m, 1H, Ar-H), 8.671-8.677 (m, 1H, Ar-H).
81% With ammonia In water at 20℃; for 1 h; General Procedure VII-BFA mixture of compound VII-XIVb (4 g, 15.7 mmol) in 40 mL of aqueous ammonia was stirred at r.t. for 1 h. Then the mixture was poured into water, the precipitate solid was collected by filtration, and dried to afford compound VII-XIVc (3 g, yield 81percent). MS (ESI) m/z (M+H)+ 237.
80%
Stage #1: With ammonium hydroxide In tetrahydrofuran; water; toluene at -10℃; for 1 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene
EXAMPLE 17A-1
2-chloro-5-nitrobenzenesulfonamide
To a solution of thionyl chloride (240 mL) and 2-chloro-5-nitro-benzenesulfonic acid (104 g, 437.6 mmol) was added N,N-dimethylformamide (2 mL) and the reaction mixture was heated up to reflux for 4 hours.
The reaction mixture was then carefully quenched into water and the product was isolated by filtration.
The sulfonyl chloride 2 was then dissolved in toluene and added to a mixture of NH4OH (520 mL) and tetrahydrofuran (520 mL) at -10° C.
After mixing for 1 h, the reaction was quenched by addition of 6 M HCl to a final pH of 4.
The layers were separated and the organic layer was concentrated to a slush.
Pentane was added and the product was isolated by filtration and dried to give the title compound (82.6 g, 80percent).
80%
Stage #1: With ammonium hydroxide In tetrahydrofuran; toluene at -10℃; for 1 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene
To a solution of thionyl chloride (240 mL) and 2-chloro-5-nitro-benzenesulfonic acid (104 g, 437. 6 mmol) was added N, N-DIMETHYLFORMAMIDE (2 ML) and the reaction mixture was heated up to reflux for 4 hours. The reaction mixture was then carefully quenched into water and the product was isolated by filtration. The sulfonyl chloride 2 was then dissolved in toluene and added to a mixture OF NH40H (520 mL) and tetrahydrofuran (520 ML) at-10 °C. After mixing for 1 h, the reaction was quenched by addition of 6 M HC1 to a final pH of 4. The layers were separated and the organic layer was concentrated to a slush. Pentane was added and the product was isolated by filtration and dried to give the title compound (82.6 g, 80percent).
55% With ammonium hydroxide In water for 18 h; Sodium nitrite (4.96 g; 72 mmol) dissolved in water (11 mL) was added drop wise over 30 minutes to a cooled solution (−5° C.) of 2-chloro-5-nitroaniline (1; 10.00 g; 58 mmol) in 12M HCl (104 mL). While stirring at −5° C. for a further 30 minutes, a solution of copper(II) chloride dissolved in water (4 mL) was poured into acetic acid (110 mL) previously saturated with sulphur dioxide (gas). This was then added to the diazonium salt 2 solution and stirred until nitrogen gas ceased to evolve. The reaction mixture was quenched with ice-water and the subsequent precipitate formed was collected by filtration and washed with cold water. Aqueous ammonium hydroxide (35percent) (120 mL) was added to the resulting sulfonyl chloride 3 and stirred for 18 hours. The solution was then filtered and the resulting filtrate was acidified using 12M HCl to precipitate the title compound 4 (7.55 g; 55percent over 3 steps). M.p 186-187° C. (lit. 177-179° C.)

Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 18 - 26
[2] Patent: US2011/152246, 2011, A1, . Location in patent: Page/Page column 293
[3] Patent: US2005/107364, 2005, A1, . Location in patent: Page/Page column 75
[4] Patent: WO2005/19191, 2005, A2, . Location in patent: Page/Page column 151
[5] Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 5, p. 669 - 680
[6] Patent: US2016/102051, 2016, A1, . Location in patent: Paragraph 0069-0070
[7] Patent: WO2008/73987, 2008, A1, . Location in patent: Page/Page column 50
[8] Justus Liebigs Annalen der Chemie, 1891, vol. 265, p. 92
[9] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3701 - 3709
[10] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3928 - 3936
[11] Patent: US2009/62263, 2009, A1, . Location in patent: Page/Page column 19-20
[12] Patent: US6818765, 2004, B1, . Location in patent: Page column 3-4; 5-7
[13] Patent: WO2010/42834, 2010, A1, . Location in patent: Page/Page column 34-35
[14] Patent: WO2008/124450, 2008, A1, . Location in patent: Page/Page column 68-69
[15] Patent: WO2013/156861, 2013, A2, . Location in patent: Page/Page column 18; 19
[16] Chinese Journal of Chemistry, 2016, vol. 34, # 11, p. 1135 - 1142
[17] Patent: WO2016/198374, 2016, A1, . Location in patent: Page/Page column 107
[18] Patent: WO2007/150001, 2007, A1, . Location in patent: Page/Page column 112
[19] Patent: WO2007/150001, 2007, A1, . Location in patent: Page/Page column 54; 112
[20] Patent: US2008/227774, 2008, A1, . Location in patent: Page/Page column 23
  • 3
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  • [ 96-72-0 ]
Reference: [1] Pharmacy and Pharmacology Communications, 2000, vol. 6, # 2, p. 89 - 95
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3928 - 3936
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3701 - 3709
[4] Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 5, p. 669 - 680
[5] Patent: US2010/9974, 2010, A1, . Location in patent: Page/Page column 13-14
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3247 - 3256
[7] Patent: WO2013/156861, 2013, A2,
[8] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8736 - 8745
[9] Patent: US2016/102051, 2016, A1,
  • 4
  • [ 96-73-1 ]
  • [ 96-72-0 ]
YieldReaction ConditionsOperation in experiment
42.4%
Stage #1: With thionyl chloride In N,N-dimethyl-formamideHeating / reflux
Stage #2: With ammonia In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene at -10℃; for 2 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene
To a solution of thionyl chloride (11 mL) and 2-chloro-5-nitro- benzenesulfonic acid (4.78 g, 20.1 mmol) was added N,N-dimethylformamide (0.92 μL) and the reaction mixture was heated to reflux for 4 h. Upon cooling, the reaction mixture was azeotroped with toluene (2-3 x). The sulfonyl chloride was dissolved in a minimal amount of toluene and then added to a mixture of concentrated aqueous ammonium hydroxide solution (25 mL) and tetrahydrofuran (25 mL) at -10 0C. After stirring for 2 h the reaction was quenched by adding a 6.0 M aqueous hydrochloric acid solution until pH 4 was reached. The layers were separated and the organic layer was concentrated in vacuo to a slurry. Pentane was added and the product was isolated by vacuum filtration to afford the desired product, 2-chloro-5- nitrobenzenesulfonamide (2.0 g, 8.48 mmol, 42.4percent) as a solid
42.4%
Stage #1: With thionyl chloride In N,N-dimethyl-formamide for 4 h; Heating / reflux
Stage #2: With ammonia In tetrahydrofuran; water; toluene at -10℃; for 2 h;
[0295] 2-Chloro-5-nitrobenzenesulfonamide owo .,X; To a solution of thionyl chloride (11 mL) and 2-chloro-5-nitro- benzenesulfonic acid (4.78 g, 20.1 mmol) was added N,N-dimethylformamide (0.92 mL) and the reaction mixture was heated to reflux for 4 h. The reaction mixture was then carefully quenched by pouring it into water and the product was isolated by vacuum filtration. The sulfonyl chloride was dissolved in a minimal amount of toluene and the added to a mixture of concentrated aqueous ammonium hydroxide solution (25 mL) and tetrahydrofuran (25 mL) at -10 °C. After stirring for 2 h the reaction was quenched by adding a 6.0 M aqueous hydrochloric acid solution until pH 4 was reached. The layers were separated and the organic layer was concentrated in vacuo to a slurry. Pentane was added and the product was isolated by vacuum filtration to afford 2-chloro-5-nitrobenzenesulfonamide (2.0 g, 42.4percent) as a solid.
3.91 g
Stage #1: for 3.5 h; Reflux
Stage #2: With ammonium hydroxide In tetrahydrofuran; toluene at 0 - 20℃;
2-chloro-5-nitrobenzenesulfonic acid (44 mmol) was heated at reflux for 3.5 hours in a mixture of thionyl chloride (22 mL) and dimethylformamide (2 mL). After cooling the reaction mixture to room temperature, the solvents were removed under high vacuum. The crude solid was azeotroped with toluene (3×100 mL) to dryness under vacuum. The final residue was taken up in a mixture of toluene (20 mL) and tetrahydrofuran (50 mL) then cooled to 0° C. Ammonia (50 mL) was added to the stirred reaction mixture, then allowed to warns to room temperature overnight. The solution was acidified using 6 M HCl (pH 4) and extracted with ethyl acetate (3×100 mL). The combined organics were dried over MgSO4, filtered and then concentrated to dryness under vacuum to yield 2-Chloro-5-nitrobenzenesulfonamide as a light brown solid (3.91 g, 38percent over 2 steps).
Reference: [1] Patent: WO2008/73982, 2008, A2, . Location in patent: Page/Page column 68
[2] Patent: WO2008/82725, 2008, A1, . Location in patent: Page/Page column 127; 171
[3] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 18 - 26
[4] Patent: WO2008/124450, 2008, A1,
[5] Patent: US2016/102051, 2016, A1, . Location in patent: Paragraph 0091; 0093
[6] Patent: WO2007/150001, 2007, A1,
[7] Patent: WO2008/73987, 2008, A1,
[8] Patent: US2008/227774, 2008, A1,
  • 5
  • [ 6283-25-6 ]
  • [ 96-72-0 ]
Reference: [1] Patent: US6242443, 2001, B1,
  • 6
  • [ 7790-94-5 ]
  • [ 100-00-5 ]
  • [ 96-72-0 ]
YieldReaction ConditionsOperation in experiment
29%
Stage #1: at 120℃; for 100 h;
Stage #2: With ammonia In water at 0 - 25℃; for 18 h;
-Chloronitrobenzene (10 g, 63.5 mmol) was charged into a flask, followed by addition of chlorosulfonic acid (21.1 mL, 317 mmol), and heated at 120 0C for 100 h. The reaction mixture was quenched by pouring it into ice (300 mL) containing a 8.0 ν <n="70"/>aqueous ammonium hydroxide solution (200 mL), and the mixture was allowed to stir at 25 0C for 18 h. The desired product was extracted with ethyl acetate (400 mL) and filtered through Merck silica gel 60, 40-63 μm and concentrated in vacuo. The crude product was slurried in toluene (70 mL) at 70 0C for 2 h before filtering to afford the desired product, 2-chloro-5-nitro-benzenesulfonamide (4.75 g, 20.1 mmol, 29percent) as a dark, brown solid. 1H NMR (400 MHz, DMSCW6) δ: 7.94 (d, IH, / = 8.8 Hz), 7.97 (bs, 2H), 8.40 (dd, IH, J1 = 8.6 Hz, J2 = 3.1 Hz), 8.64 (d, IH, / = 3.1 Hz).
Reference: [1] Patent: WO2008/73982, 2008, A2, . Location in patent: Page/Page column 68-69
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5647 - 5647
  • 7
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  • [ 96-72-0 ]
Reference: [1] Patent: US2011/152246, 2011, A1,
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 18 - 26
[3] RSC Advances, 2016, vol. 6, # 27, p. 23038 - 23047
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