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CAS No. :77815-14-6 MDL No. :MFCD01086598
Formula : C9H7FN2S Boiling Point : -
Linear Structure Formula :- InChI Key :WSOKJBHBMAGBIP-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :722371
Synonyms :

Safety of [ 77815-14-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H320-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 77815-14-6 ]

* 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.

  • Downstream synthetic route of [ 77815-14-6 ]

[ 77815-14-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 403-42-9 ]
  • [ 17356-08-0 ]
  • [ 77815-14-6 ]
YieldReaction ConditionsOperation in experiment
90% With iodine; triethylamine sulfate In neat (no solvent) at 40℃;
87% With iodine at 100℃;
75% With carbon tetrabromide; triethylamine In acetonitrile at 20℃; for 6h; General procedure for the synthesis of 2-aminothiazoles 3 General procedure: To a mixture of ketone (0.5 mmol), thiourea (0.5 mmol), and triethylamine (0.5 mmol) in acetonitrile (3 mL) was added carbon tetrabromide (0.5 mmol) in a round bottom flask at room temperature and the reaction mixture was stirred for 2-6 h. After completion of the reaction (monitored by TLC), water (5 mL) was added and the mixture was extracted with EtOAc (3*5 mL). The combined organic phase was dried over MgSO4, filtered, and evaporated under reduced pressure to give the crude product. The resulting product was purified by silica gel column chromatography using a gradient mixture of hexane/ethyl acetate as eluent to afford an analytically pure sample of 3.
75% With bromine In ethanol for 11h; Reflux;
69% With iodine at 100℃; for 8h; 4.1.2. General procedure for synthesis of 2-amino-4-(substituted phenyl)-1,3-thiazoles (3a-k) General procedure: A mixture of thiourea (50 mmol), the corresponding acetophenone (25 mmol) and iodine (25 mmol) is stirred at 100 °C for 8 h.Then the reaction mixture is cooled, extracted with diethyl ether toremove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole. The crude product is purified by recrystallization from alcohol.
68% Stage #1: 1-(4-fluorophenyl)ethanone; thiourea In propan-1-ol for 2h; Reflux; Stage #2: With pyridine In propan-1-ol for 5h; Reflux;
58% With iodine at 100℃; for 2h;
55% With iron(III) chloride hexahydrate; iodine at 110℃; for 24h; Sealed tube; Green chemistry;
55% With iodine; dimethyl sulfoxide at 80℃; for 12h; Schlenk technique; I2-catalyzed coupling reaction of ketones and thiourea: general procedure General procedure: A Schlenk tube (20 mL) was charged with ketone 1 (4 mmol),thiourea (2) (2 mmol), I2 (0.4 mmol) and DMSO (4 mL). Thetube was sealed with a rubber septum and the reaction mixturewas stirred at 80 °C for 12 h. After completion of thereaction, the mixture was cooled to room temperature. Ethylacetate (20 mL) and a saturated solution of NaHCO3 (20 mL)were added and the organic layer was separated. The aqueousphase was extracted with ethyl acetate (3 × 10 mL). Thecombined organic layer was washed with a saturated solutionof NaCl (20 mL) and then dried over anhydrous Na2SO4.After filtration, the solvent was removed under reduced pressure.The crude mixture was purified by chromatography onsilica gel to yield the desired products.
54.5% With iodine In dimethyl sulfoxide at 80℃; for 12h; 2; 18 Example 2 Add 0.553 g (4 mmol) of p-fluoroacetophenone to the reaction tube containing the stirring magnet.Thiourea 0.152g (2mmol),0.051 g (0.4 mmol) of iodine and 4 ml of DMSO.Place the reaction tube in an oil bath at 80 ° C.The reaction was stirred for 12 h.After the reaction, the reaction solution was treated with a saturated NaHCO3 solution (20 mL).An additional 30 ml of water was added and extracted three times with 20 mL of ethyl acetate.The extract was washed with water and saturated NaCl solution, and dried over anhydrous Na2SO4.The solvent was removed under reduced pressure on a rotary evaporator, and the residue was separated by silica gel column chromatography.Eluted with petroleum ether / ethyl acetate (5: 1 by volume),To give 2-amino-4-p-fluorophenylthiazole (0.212 g),The yield was 54.5%.
With iodine
With bromine 1.) dioxane, dichloroethane, 2 h: 60-70 deg C, 4 h: reflux; 2.) 2 h: 60-70 deg C, 4 h: reflux; Multistep reaction;
With iodine for 8h; Reflux;
With iodine at 120℃; for 4h;
With iodine at 120℃; for 4h;
With halogen for 24h; Reflux;
With iodine at 100℃; for 8h; General procedure for synthesis of 2-amino-4-(substituted-phenyl)-1,3-thiazoles General procedure: A mixture of thiourea (7, 50 mmol), the corresponding acetophenone (6, 25 mmol) and iodine(25 mmol) is stirred at 100 °C for 8 h. Then the reaction mixture is cooled, extracted with diethylether to remove excess of acetophenone, and then washed with aqueous sodium thiosulfate to remove excess iodine and later with cold water. The crude product is dissolved in hot water, filtered to remove sulphone, and the filtrate is basified with aqueous Na2CO3 to yield the corresponding 2-amino-4-(substituted-phenyl)-1,3-thiazole (5). The crude product is purified by recrystallization from alcohol. The synthesis and spectral data of compounds 5a-i have been reported by us earlier [2]. The data in respect of compounds 5j-l is described here.
Stage #1: 1-(4-fluorophenyl)ethanone; thiourea With bromine In ethanol for 2h; Stage #2: In ethanol for 12h; Reflux;
With bromine Reflux;
With iodine at 100℃; 4.1.2. General procedure for preparation of aminothiazoleintermediates 9a-r General procedure: A mixture of the appropriate aryl ketones, 1-cyclobutylethan-1-one or 1-(furan-2-yl)ethan-1-one (8a-r, 0.1 mol) and thiourea(0.20 mol), and iodine (0.1 mol) were heated for 5 h to thick mass at100 C. After the thick mass was cooled, methanol was added, thesolid was treated with water and filtered. The residue was dried invacuo yielding the hydriodide salt of the aminothiazole intermediates9a-r, which was suitable for use in the next reaction.
With bromine Synthesis of 4-(4-substituted phenyl)thiazol-2-amines(4a-f): General procedure: General procedureVarious 4-(4-substituted phenyl)thiazol-2-amines were synthesized form acetophenone, thiourea, and bromine.
With iodine In ethanol Reflux;
With sodium iodide dichloride In tetrahydrofuran; water for 12h; Reflux; General procedure for the synthesis of 3a General procedure: To a stirred solution of thiourea (0.002 mol, 0.15 g), and ketone (0.001 mol, 0.12 g) in THF (10 mL) at room temperature was slowly added aq. NaICl2 (0.0005 mol, 0.11 ml, 30%w/w aqueous NaICl2).[61] The resultant reaction mixture was refluxed for 12 h. After completion of reaction (TLC), thesolvent was evaporated under the vacuum. Then the resulted residue was diluted with water and extracted with ethyl acetate.The organic layer was separated and washed successivelywith of 10% sodium bisulfate solution (5 mL), 10% sodium bicarbonate (3 mL) of water. The organic layer was driedover anhydrous sodium sulfate and concentrated under thereduced pressure to give the crude product. Pure product was obtained after silica gel column chromatography with 30% EtOAc-Hexane.

Reference: [1]Kakati, Praachi; Singh, Preeti; Yadav, Priyanka; Awasthi, Satish Kumar [New Journal of Chemistry, 2021, vol. 45, # 15, p. 6724 - 6738]
[2]Siddiqui, Hamid Latif; Iqbal, Amjid; Ahmad, Saeed; Weaver, George W. [Molecules, 2006, vol. 11, # 2-3, p. 206 - 211]
[3]Keshari, Twinkle; Kapoorr, Ritu; Yadav, Lal Dhar S. [Tetrahedron Letters, 2015, vol. 56, # 41, p. 5623 - 5627]
[4]Ge, Lingqing; Hu, Qiaozhen; Shi, Mengrao; Yang, Huiyun; Zhu, Guoji [RSC Advances, 2017, vol. 7, # 52, p. 32909 - 32922]
[5]Koppireddi, Satish; Komsani, Jayaram Reddy; Avula, Sreenivas; Pombala, Sujitha; Vasamsetti, Satishbabu; Kotamraju, Srigiridhar; Yadla, Rambabu [European Journal of Medicinal Chemistry, 2013, vol. 66, p. 305 - 313]
[6]Alagarsamy; Senthilraja; Raja Solomon [Journal of Heterocyclic Chemistry, 2016, vol. 53, # 5, p. 1635 - 1639]
[7]Zitko, Jan; Jand'Ourek, Ondřej; Paterová, Pavla; Navrátilová, Lucie; Kuneš, Jiří; Vinšová, Jarmila; Doležal, Martin [MedChemComm, 2018, vol. 9, # 4, p. 685 - 696]
[8]Ujwaldev, Sankuviruthiyil M.; Harry, Nissy Ann; Neetha, Mohan; Anilkumar, Gopinathan [Journal of Heterocyclic Chemistry, 2021, vol. 58, # 2, p. 646 - 653]
[9]Zhang, Qian; Wu, Jiefei; Pan, Zexi; Zhang, Wen; Zhou, Wei [Journal of Chemical Research, 2021, vol. 45, # 1-2, p. 89 - 94]
[10]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN110845437, 2020, A Location in patent: Paragraph 0030-0035; 0126-0129
[11]Joshi,K.C.; Bahel,S.C. [Journal of the Indian Chemical Society, 1962, vol. 39, p. 121 - 128] Bhargava; Lakhan; Tripathi [Journal of the Indian Chemical Society, 1982, vol. 59, # 6, p. 773 - 775]
[12]Cousse; Mouzin; Bonnaud; Tarayre; Couzinier [Arzneimittel-Forschung/Drug Research, 1986, vol. 36, # 9, p. 1391 - 1393]
[13]Location in patent: experimental part More; Lawand; Dalave; Nalawade [Journal of the Indian Chemical Society, 2008, vol. 85, # 8, p. 862 - 865]
[14]Location in patent: scheme or table Thumar, Nilesh J.; Patel, Manish P. [Archiv der Pharmazie, 2011, vol. 344, # 2, p. 91 - 101]
[15]Thumar, Nilesh J.; Patel, Manish P. [Journal of Heterocyclic Chemistry, 2012, vol. 49, # 5, p. 1169 - 1178]
[16]Joshi, Shrinivas D.; More, Uttam A.; Dixit, Sheshagiri R.; Korat, Haresh H.; Aminabhavi, Tejraj M.; Badiger, Aravind M. [Medicinal Chemistry Research, 2014, vol. 23, # 3, p. 1123 - 1147]
[17]Koppireddi, Satish; Chilaka, Deepika Raj Kumari; Avula, Sreenivas; Komsani, Jayaram Reddy; Kotamraju, Srigiridhar; Yadla, Rambabu [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5428 - 5431]
[18]Zhao, Gang; Lan, Dengzhe; Qi, Guobao [Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 778 - 790]
[19]Wang, Xiwen; Yi, Yuexiong; Lv, Qiongying; Zhang, Juan; Wu, Kejia; Wu, Wanrong; Zhang, Wei [Chemical Biology and Drug Design, 2018, vol. 91, # 3, p. 728 - 734]
[20]Chen, Lingfeng; Chen, Hongjin; Chen, Pengqin; Zhang, Wenxin; Wu, Chao; Sun, Chuchu; Luo, Wu; Zheng, Lulu; Liu, Zhiguo; Liang, Guang [European Journal of Medicinal Chemistry, 2019, vol. 161, p. 22 - 38]
[21]Monga, Vikramdeep; Singh, Hargyan; Singh, Gurpreet [Indian Journal of Heterocyclic Chemistry, 2017, vol. 27, # 1, p. 51 - 57]
[22]Gobala Krishnan; Gnanaprakash; Chandrasekhar [International Journal of Research in Pharmaceutical Sciences, 2019, vol. 10, # 2, p. 1504 - 1509]
[23]Poola, Sreelakshmi; Gundluru, Mohan; Nadiveedhi, Maheshwara Reddy; Saddala, Madhu Sudhana; P. T. S. R. K, Prasada Rao; Cirandur, Suresh Reddy [Phosphorus, Sulfur and Silicon and the Related Elements, 2020, vol. 195, # 5, p. 409 - 420]
  • 2
  • [ 17356-08-0 ]
  • [ 456-04-2 ]
  • [ 77815-14-6 ]
YieldReaction ConditionsOperation in experiment
85% With Saccharomyces cerevisiae In acetonitrile at 25℃; for 4h; Green chemistry;
78% In ethanol
  • 3
  • [ 395-44-8 ]
  • [ 77815-14-6 ]
  • [ 1048643-71-5 ]
YieldReaction ConditionsOperation in experiment
37% A mixture of 2-amino-4-(4-fluorophenyl)thiazole (0.39 g, 2.00 mmol), 2- (trifluoromethyl)benzyl bromide (0.48 g, 2.00 mmol) and potassium carbonate (0.56 g, 4.00 mmol) in acetonitrile (20 mL) was refluxed for 16 h. After the reaction mixture was cooled to ambient temperature, it was diluted with water (2.0 mL) and neutralized with <n="85"/>10% aqueous hydrochloric acid solution (2.0 ml_). The reaction mixture was extracted with ethyl acetate (3 x 20.0 mL). The combined organic layer was washed with water (2 x 50.0 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography eluting with ether in hexane (3:7) to afford [4-(4-fluorophenyl)thiazol-2- yl]-(2-trifluoromethylbenzyl)amine (0.26 g, 37%) as a brown gummy material: 1H NMR (300 MHz, CDCI3) delta 7.84-7.80 (m, 2H), 7.45 (d, J = 11.7 Hz, 2H), 7.41-7.21 (m, 3H), 7.05-6.98 (m, 2H), 6.66 (s, 1 H), 4.87 (s, 2H); 13C NMR (75 MHz, CDCI3) delta 170.1 , 164.1 , 160.8, 150.8, 147.6, 131.2, 129.1 , 127.8, 127.0, 122.3, 120.6, 118.9, 115.4, 100.9, 49.2.
  • 4
  • [ 776-04-5 ]
  • [ 77815-14-6 ]
  • [ 1048643-77-1 ]
YieldReaction ConditionsOperation in experiment
24% With triethylamine; In dichloromethane; at 20℃; for 16h; To a solution of 2-amino-4-(4-fluorophenyl)thiazole (0.50 g, 2.57 mmol) in dichloromethane (50.0 mL) was added triethylamine (1.2 mL) followed by addition of 2- (trifluoromethyl)benzenesulfonyl chloride (0.79 g, 3.22 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The mixture was washed with water (2 x 50.0 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dryness. The residue was crystallized from ethyl acetate in hexane to afford lambda/-[4-(4-fluorophenyl)thiazol-2-yl]-2- trifluoromethylbenzenesulfonamide (0.25 g, 24%) as a colourless solid: Rf = 0.60 (ethyl acetate in hexane, 1 :1 ); mp > 200 0C; 1H NMR (300 MHz, acetone-d6) delta 9.49 (br, 1 H), 8.29 (d, J = 7.5 Hz, 1 H), 7.91-7.84 (m, 2H), 7.80 (d, J = 7.5 Hz, 1 H), 7 '.72-7 '.61 (m, 2H), 7.26-7.19 (m, 3H); 13C NMR (75 MHz, DMSO-d6) delta 172.9, 166.7, 163.4, 144.7, 139.8, 133.1 , 131.7, 131.1 , 129.6, 128.5 (m), 126.8, 126.2 (m), 117.5, 103.4; MS (ES+) <n="88"/>m/z 403 (M + 1 ).
  • 5
  • [ 16588-74-2 ]
  • [ 77815-14-6 ]
  • [ 438243-39-1 ]
YieldReaction ConditionsOperation in experiment
92% In 1,4-dioxane at 20℃; for 16h; 25 To a solution of 2-amino-4-(4-fluorophenyl)thiazole (0.54 g, 2.00 mmol) in dioxane (20.0 ml.) was added 3,5-bis(trifluoromethyl)phenyl isocyanate (1.04 g, 4.08 mmol), followed by catalytic amount of triethyl amine (0.2 ml_). The pale yellow reaction solution was stirred at ambient temperature for 16 h, upon which time precipitate was formed. After removing the solvent under reduced pressure, the residue was crystallized from ether to afford 1-(3,5-t»/s-trifluoromethylphenyl)-3-[4-(4- fluorophenyl)thiazol-2-yl]urea (0.83 g, 92%) as a colourless solid: Rf = 0.33 (diethyl ether in hexane, 1 :1 ); mp > 260 0C; 1H NMR (300 MHz, acetone-cf6) δ 10.30 (br, 1 H), 9.22 (br, 1H), 8.23 (s, 1 H), 8.19 (s, 1 H), 7.99-7.87 (m, 2H), 7.67 (d, J = 10.2 Hz, 1H), 7.43 (s, 1 H), 7.21-7.08 (m, 2H); 13C NMR (75 MHz, acetone-d6) δ 164.0, 160.8, 159.2, 151.5, 148.6, 141.4, 141.0, 132.0, 131.9, 131.5, 131.4, 131.1 , 127.8, 127.7, 125.3, 121.7, 118.7, 115.8 (m), 115.4, 115.1 , 106.8; MS (ES+) m/z 450 (M + 1 ).
  • 6
  • [ 3261-87-8 ]
  • [ 77815-14-6 ]
  • 2-((2-((5-(4-fluorophenyl)thiazol-2-yl)amino)-2-oxoethyl)thio)acetic acid [ No CAS ]
  • 7
  • [ 459-47-2 ]
  • [ 17356-08-0 ]
  • [ 77815-14-6 ]
YieldReaction ConditionsOperation in experiment
87% Add 3 mL of water to a 25 mL reaction flask and add 0.50 mmol in sequence.<strong>[459-47-2]1-ethyl-4-fluorobenzene</strong>, 0.75 mmol DBH and 0.05 mmol TBHP were reacted at 60 C for 4 h. After cooling, 1.50 mmol of sodium hydrogencarbonate and 0.50 mmol of thiourea were added in sequence, and the reaction was continued at 80 C for 1 h. Extraction with ethyl acetate, concentration of the organic phase, column chromatography to give 84 mg whiteSolid, yield 87%.
84% Add 3 mL of water and 30 μL of Tween in a 25 mL reaction flask. 0.5 mmol of <strong>[459-47-2]1-ethyl-4-fluorobenzene</strong>, 1.5 mmol of NBS and 0.05 mmol of AIBN, The reaction was carried out at 60 C for 4 h, and after the reaction was completed, it was cooled. Then 1.5 mmol of cesium carbonate and 0.5 mmol of thiourea were added in sequence. After reacting at 80 C for 1 h, ethyl acetate was added after the reaction. Extracted with saturated brine and concentrated organic phase. Column chromatography gave 81 mg of a white solid (yield: 84%).
  • 8
  • [ 412923-44-5 ]
  • [ 77815-14-6 ]
YieldReaction ConditionsOperation in experiment
61.9% With ammonium hydroxide; copper(II) bromide In lithium hydroxide monohydrate at 100℃; for 12h; Inert atmosphere; 6 Using 2.57g (1moL) 2-bromo-5-(4-fluorophenyl)thiazole and 10ml ammonia water as raw materials, using 0.14g (0.1moL) cuprous bromide as a catalyst, in 10ml deionized water, under nitrogen protection, the reaction was carried out for 12 h under the stirring conditions of controlled temperature of 100 °C and pH of 8-9, and the rotation speed was 500 r/min; wherein the compound represented in the general formula (I): ammoniacal liquor: monovalent copper salt: the feeding ratio of water is 1mol:10ml:0.1mol:10ml. After the TLC monitoring reaction was completed, the reaction solution was cooled to 25° C., 250 ml of deionized water was added, and the filtration with a pore size of 30 μm was carried out to remove the solid component, that is, the unreacted and water-insoluble general formula (I) and a small amount of catalyst, Until there is no product in the filter cake, the filtrate is obtained; After collecting the filtrate, extract the product three times with 100 ml of ethyl acetate, combine the organic phases to obtain an ethyl acetate phase, and then wash it once with 100 ml of saturated brine to complete the extraction and washing to obtain washed ethyl acetate, mutually; finally, the washed ethyl acetate phase was dried over anhydrous sodium sulfate and concentrated in a rotary evaporator to obtain 1200 mg of 2-amino-4-tert-butylthiazole
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