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[ CAS No. 315228-79-6 ] {[proInfo.proName]}

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Chemical Structure| 315228-79-6
Chemical Structure| 315228-79-6
Structure of 315228-79-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 315228-79-6 ]

CAS No. :315228-79-6 MDL No. :MFCD11845316
Formula : C8H4N2S2 Boiling Point : -
Linear Structure Formula :- InChI Key :XRIDVJQTZRUCDJ-UHFFFAOYSA-N
M.W : 192.26 Pubchem ID :22029197
Synonyms :

Calculated chemistry of [ 315228-79-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.59
TPSA : 103.72 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 3.36
Consensus Log Po/w : 2.21

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.223 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (Ali) : -3.95
Solubility : 0.0216 mg/ml ; 0.000112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.17
Solubility : 0.13 mg/ml ; 0.000678 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.12

Safety of [ 315228-79-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 315228-79-6 ]

* 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 [ 315228-79-6 ]
  • Downstream synthetic route of [ 315228-79-6 ]

[ 315228-79-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 140-89-6 ]
  • [ 33348-34-4 ]
  • [ 315228-79-6 ]
YieldReaction ConditionsOperation in experiment
98% With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In N,N-dimethyl-formamide at 110℃; for 10 h; Inert atmosphere; Sealed tube General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.
82.1% With copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 6 h; Inert atmosphere; Sealed tube General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110°C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1–S13).
Reference: [1] Synthetic Communications, 2015, vol. 45, # 20, p. 2378 - 2385
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 5, p. 699 - 701
  • 2
  • [ 75-15-0 ]
  • [ 33348-34-4 ]
  • [ 315228-79-6 ]
YieldReaction ConditionsOperation in experiment
45% With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 110℃; for 12 h; Sealed tube; Inert atmosphere General procedure: A sealed tube (50 mL) was charged with 2-haloaniline 1a (2mmol), CS2 (10 mmol), Na2S (4mmol) and DMF (2 mL) at room temperature under an argon gas atmosphere and the tube was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically at 110 °C for 12 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, 2 mL HCl (3 mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by dichloromethane (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel colum chromatography (eluent: petroleum ether / ethyl acetate) give the corresponding pure product 2a.
Reference: [1] Synthetic Communications, 2017, vol. 47, # 20, p. 1916 - 1925
  • 3
  • [ 21803-75-8 ]
  • [ 140-89-6 ]
  • [ 315228-79-6 ]
YieldReaction ConditionsOperation in experiment
84% for 4 h; Reflux Step 2: To a solution of 4-amino-3-chlorobenzonitrile (12.2 g, 80.2 mmol) from Step 1 of this Example in DMF(60 mL) was added potassium O-ethyl carbonodithioate (28.9 g, 180.7 mmol) at rt. The mixture was refluxed for 4 h.After cooling to rt, the reaction mixture was poured into ice water and acidified with 2N aq HCl. The tan solids werecollected and dried in vacuum oven overnight. Then the solids were refluxed with 500 mL of CHCl3 for 10 min. Aftercooling to rt, the mixture was treated with 200 mL of hexanes and sonicated for 20 min. The pale brown solid wascollected by filtration to give 2-mercaptobenzo[d]thiazole -6-carbonitrile (12.9 g, 84percent). 1H NMR (300 MHz, DMSO-d6)δ 14.16 (br s, 1H), 8.23 (d, J= 0.9 Hz, 1H), 7.83 (dd, J= 1.3, 8.5 Hz, 1H), 7.31 - 7.51 (m, 1H).
56% at 110℃; for 16 h; Inert atmosphere To a stirred solution of 4-annno-3-ehtorobenzonitrile (HX; 1.0 g, 6.55 mmo ) in DMF (20 mL) under argon atmosphere was added potassium O-ethylcarbonodithioate (2.62 g, 16.38 mmol)) atRT. The reaction mixture was stirred at 1 10 °C for 16 h. The reaction mixture was diluted water (30 mL) and acidified using 2iV HCi to pH=2, to obtain the solid. The solid was filtered, washed with Hexane (2 x 20 mL) and dried under reduced pressure to obtain compound HY (700 mg, 3.64 nnnoL 56percent) as yellow solid. *H NMR (500 MHz, DMSO-<): δ 14.3 (br s, 1H), S.24 (s, 1 H), 7.83 (dd, J= 8.1, 1.2 Hz, 1 H), 7.41 (d, J = 8. Hz. 1H).
Reference: [1] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 0384
[2] Patent: WO2017/117393, 2017, A1, . Location in patent: Page/Page column 260; 261
  • 4
  • [ 63069-50-1 ]
  • [ 140-89-6 ]
  • [ 315228-79-6 ]
YieldReaction ConditionsOperation in experiment
82% at 120 - 130℃; Inert atmosphere General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5–1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120–130 °C until the aniline was fully consumed (3–14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1–2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
  • 5
  • [ 75-15-0 ]
  • [ 50397-74-5 ]
  • [ 315228-79-6 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 12, p. 3202 - 3205
  • 6
  • [ 21803-75-8 ]
  • [ 315228-79-6 ]
Reference: [1] Patent: US2003/139390, 2003, A1,
  • 7
  • [ 873-74-5 ]
  • [ 315228-79-6 ]
Reference: [1] Patent: EP2766359, 2016, B1,
  • 8
  • [ 315228-79-6 ]
  • [ 80945-83-1 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 20 - 25℃; for 0.25 h; Inert atmosphere
Stage #2: at 20 - 25℃; for 3 h; Inert atmosphere
General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20–25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20–25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.
28% at 20 - 60℃; for 2 h; Inert atmosphere The mixture of compound HY (2.1 g, 10.93 mmol) in SO2O2 (20 inL) under argon atmosphere was stirred at RT for I h. The reaction mixture was stirred at 60 °C for 1 h. The progress of the reaction was monitored by TLC , The reaction mixture was diluted with ice cold water (50 mL), to obtain the solid. The solid was filtered. The crude material was purified by silica gel column chromatography (ehieiit: 10-20percent EtOAe Hexane) to afford compound HZ (600 mg, 3.08 mmol, 28percent) as an off-white solid. 3H NMR (500 MHz, DMSO-i); δ 8.70 (s, H), 7.15 (4 J = 8.5 Hz, 1H), 7.98 (dd, J = 8.5, 1.7 Hz, 1H).
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
[2] Patent: WO2017/117393, 2017, A1, . Location in patent: Page/Page column 261
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