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[ CAS No. 2766-74-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2766-74-7
Chemical Structure| 2766-74-7
Chemical Structure| 2766-74-7
Structure of 2766-74-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2766-74-7 ]

CAS No. :2766-74-7 MDL No. :MFCD00051667
Formula : C4H2Cl2O2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :SORSTNOXGOXWAO-UHFFFAOYSA-N
M.W : 217.09 Pubchem ID :2733925
Synonyms :

Calculated chemistry of [ 2766-74-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.41
TPSA : 70.76 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) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.83
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 3.41
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.42

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.102 mg/ml ; 0.000468 mol/l
Class : Soluble
Log S (Ali) : -4.07
Solubility : 0.0186 mg/ml ; 0.0000857 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.83
Solubility : 0.32 mg/ml ; 0.00148 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 2766-74-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2766-74-7 ]

* 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 [ 2766-74-7 ]
  • Downstream synthetic route of [ 2766-74-7 ]

[ 2766-74-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 96-43-5 ]
  • [ 2766-74-7 ]
YieldReaction ConditionsOperation in experiment
88% at 0 - 20℃; The following procedure was adapted from C. A. Hunt, et al. J. Med. Chem. 1994, 37, 240-247. In a three-necked R.B. flask, equipped with a mechanical stirrer, an air condenser, a dropping funnel, and a moisture-guard tube, was placed chlorosulfonic acid (240 mL, 3.594 mol). Under stirring, PCl5 (300 g, 1.44 mol, 0.40 equiv) was added in portions, over ca. 45 mins. During the addition, a large volume of HCl gas evolved vigorously,- but the temperature of the mixture did not rise significantly (<40 0C). By the time all the PCl5 had been added, an almost clear, pale yellow solution resulted, with only a few solid pieces of PCI5 floating in the suspension. It was stirred until gas evolution ceased (0.5 h).[0102] Then the reaction vessel was cooled in ice, and 2-chloro-thiophene (66.0 mL, 0.715 mol) was added via the dropping funnel, over 1.0 h. With the addition of the very first few drops of 2-Cl-thiophene, the mixture turned dark purple, and by the time all of the thiophene had been added, a dark purple solution resulted. During the addition, HCl gas evolved <n="35"/>continuously, at a slow rate. The reaction mixture was then stirred at room temperature overnight.[0103] Then the mixture, dark-purple clear solution, was added dropwise to crushed ice (3 L), over 0.5 h. On addition to ice, the purple color disappeared instantaneously; the colorless thin emulsion was stirred mechanically at room temperature for ca. 15 h. Then the mixture was extracted with CH2Cl2 (3 x 300 mL). The combined CH2Cl2-extract was washed with water (Ix 200 mL), saturated NaHCO3 (Ix 250 mL), brine (1 x 100 mL), dried (Na2SO4), and concentrated on a rotary evaporator to yield the crude product as a pale yellow glue, which showed a tendency to solidify, yielding a semi-solid mass. This was then purified by high- vacuum distillation (bp 110-112712mm) to yield 135.20 g (88percent) of the title compound as a colorless/pale-yellow semi solid.
88% at 0 - 40℃; Example 1: Synthesis of the intermediate sulfonylurea carbamate (8)Step 1 - Preparation 5-chlorothiophene-2-sulfonyl chloride: <n="64"/>[0269] The following procedure was adapted from C. A. Hunt, et al. J. Med. Chem. 1994, 37, 240-247. In a three-necked R.B. flask, equipped with a mechanical stirrer, an air condenser, a dropping funnel, and a moisture-guard tube, was placed chlorosulfonic acid (240 mL, 3.594 mol). Under stirring, PCI5 (300 g, 1.44 mol, 0.40 equiv) was added in portions, over ca. 45 mins. During the addition, a large volume of HCl gas evolved vigorously, but the temperature of the mixture did not rise significantly (<40 0C). By the time all the PCI5 had been added, an almost clear, pale yellow solution resulted, with only a few solid pieces of PCI5 floating in the suspension. It was stirred until gas evolution ceased (0.5 h). [0270] Then the reaction vessel was cooled in ice, and 2-chloro-thiophene (66.0 mL, 0.715 mol) was added via the dropping funnel, over 1.0 h. With the addition of the very first few drops of 2-Cl-thiophene, the mixture turned dark purple, and by the time all of the thiophene had been added, a dark purple solution resulted. During the addition, HCl gas evolved continuously, at a slow rate. The reaction mixture was then stirred at room temperature overnight.[0271] Then the mixture, dark-purple clear solution, was added drop wise to crushed ice (3 L), over 0.5 h. On addition to ice, the purple color disappeared instantaneously; the colorless thin emulsion was stirred mechanically at room temperature for ca. 15 h. Then the mixture was extracted with CH2Cl2 (3 x 300 mL). The combined CH2Cl2-extract was washed with water (Ix 200 mL), saturated NaHCO3 (Ix 250 mL), brine (1 x 100 mL), dried (Na2SO4), and concentrated on a rotary evaporator to yield the crude product as a pale yellow glue, which showed a tendency to solidify, yielding a semi-solid mass. This was then purified by high- vacuum distillation (bp 110-112°/12mm) to yield 135.20 g (88percent) of the title compound as a colorless/pale-yellow semi solid.
Reference: [1] Patent: WO2007/56167, 2007, A2, . Location in patent: Page/Page column 33-34
[2] Patent: WO2008/137809, 2008, A2, . Location in patent: Page/Page column 61-62
[3] Pharmazie, 1994, vol. 49, # 2-3, p. 115 - 117
[4] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 3, p. 1063 - 1064
[5] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 250,279
[6] Journal of Medicinal Chemistry, 1994, vol. 37, # 2, p. 240 - 247
[7] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 617 - 620
[8] Patent: US3996243, 1976, A,
  • 2
  • [ 2766-74-7 ]
  • [ 75-64-9 ]
  • [ 155731-14-9 ]
YieldReaction ConditionsOperation in experiment
98% at 0 - 23℃; A. Synthesis of (tert-butyl)[(5-chloro(2-thienyl))sulfonyl]amine (0316) A solution of 5.5 g (27.5 mmol) of 5-chlorothiophenesulfonyl chloride in dry THF at 0°C was treated with a solution of 5.7 mL (75.5 mmol) oft-butylamine. After warming to 23°C, the reaction mixture was diluted with 125 mL of diethyl ether, filtered, and washed with 1 N HCl, brine, and dried (MgSO4). Concentration in vacuo affords 6.4 g (98percent) of the named compound as an oil.
Reference: [1] Patent: EP2314593, 2016, B1, . Location in patent: Paragraph 0316
[2] Pharmazie, 1994, vol. 49, # 2-3, p. 115 - 117
[3] Patent: US2002/77486, 2002, A1,
[4] Patent: US6906063, 2005, B2,
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