Name: 1643-15-8|2-(m-Tolyloxy)acetic acid|98%
Brand: Ambeed
SKU: A566478
Price: 10.0 USD
Availability: InStock
Rating: 95 (29 reviews)

1
[ 110-86-1 ]
[ 1643-15-8 ]
[ 54914-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide at 30℃; Electrolysis;

Reference： [1]Fichter; Kestenholz [Helvetica Chimica Acta, 1942, vol. 25, p. 785,791]

2
[ 67-56-1 ]
[ 1643-15-8 ]
[ 63051-20-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With toluene-4-sulfonic acid at 25℃; for 2h;
	With hydrogenchloride
	With toluene-4-sulfonic acid at 25℃; for 3h;

Reference： [1]Del Carmen Cruz, María; Tamariz, Joaquín [Tetrahedron, 2005, vol. 61, # 42, p. 10061 - 10072]
[2]Forte [Gazzetta Chimica Italiana, 1892, vol. 22 II, p. 543]
[3]Cruz, María Del Carmen; Tamariz, Joaquín [Tetrahedron Letters, 2004, vol. 45, # 11, p. 2377 - 2380]

3
[ 1643-15-8 ]
[ 40926-72-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With thionyl chloride In benzene for 3h; Reflux;
	With thionyl chloride
	With thionyl chloride In ethyl acetate; benzene for 8h; Heating;

	With thionyl chloride In methanol; ethyl acetate for 7h; Heating;
	With thionyl chloride In methanol; ethyl acetate; benzene for 8h; Heating;
	With thionyl chloride for 8h; Heating;
	With thionyl chloride In benzene for 1h; Heating;
	With thionyl chloride In chloroform Heating;
	With thionyl chloride In benzene Heating;
	With thionyl chloride In hexane Heating;
	With thionyl chloride for 12h;	18.1 Excess thionyl chloride was added to two equivalents of substituted phenoxyacetic acid and was stirred for 12h. The reaction was concentrated and the corresponding acid chloride was added to a solution of one equivalent aromatic diamine and two equivalent of diisopropylethyl amine in anhydrous methylene chloride and stirred for 12 h. The reaction mixture was washed with IN HCI, 10% w/w NaHC03 and dried (MgS04), and concentrated in vacuo. The crude reaction was purified by flash chromatography (Si02, methylene chloride/methanol (98:2). The product identity and purity was confirmed by electrospray LC-MS using method A.
	With thionyl chloride
	With thionyl chloride at 80℃; for 4h;	3.1. Synthesis of the compound 3 series General procedure: The intermediates 2 were synthesized via methods reported previously.17 Compounds 2 (20 mmol) and thionyl chloride (15 mL, 200 mmol) were added to a 50 mL round-bottomed flask, the mixture was refluxed for 4 h, and then thionyl chloride was evaporated at reduced pressure. Anhydrous toluene (10 mL) was added to the acyl chloride, and the yielded solution was added dropwise to aqueous ammonia (10 mL) in a 100 mL three-necked flask equipped with a drying tube at 0-5 °C. The mixture was stirred at that temperature for another 1.5 h. After filtration the solvent was removed, the remaining residue was solved in hot acetone, the insoluble was discarded. Crude product was obtained by evaporating the solvent and purified by recrystallization from ethanol-water to obtain compounds 3.
	With thionyl chloride for 6h; Reflux;
	With thionyl chloride for 4h; Reflux;	General Procedure forSynthesis of Compounds 51-54 General procedure: Phenoxyaceticacids (50 mmol) was added to thionylchloride (50 mL) at room temperature under a calcium chloride tube.The mixture was then heated under reflux for 4 h. After cooling to roomtemperature, the mixture was evaporated in vacuo. The residue was dissolved in50 mL of dichloromethaneand aluminium chloride (13 g, 98 mmol) was addedslowly to the solution at 0°C. After stirring at 0°C for 15min, the reactionstirred at room temperature for 30min. The mixture was then poured into icewater, extracted with portions of ethyl acetate (3×50 mL). The organic layerwas washed with brine, dried over anhydrous sodium sulfate and the solventremoved in vacuo. The residue was purified by column chromatography to get theproduct.
	With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 50℃; for 5h;	General procedure for the synthesis of HY-1a-HY-1f General procedure: A mixture of aryloxyl acid (5a-f) (10 mmol), thionyl chloride(15 mmol), tetrahydrofuran (50 ml) and dimethylformamide(1 ml) was stirred at 50 C for 5 h. Then tetrahydrofuran and thionylchloride were removed in vacuo. Yellow liquid (6a-f) obtainedand pyridine (2.5 ml) were then added to a solution of 10 (10 mmolin 25 ml tetrahydrofuran). The solution was stirred at 50 C for 3 h.When the reaction was completed, the solution was poured intohydrochloric acid (1 mol/L) and extracted with CH2Cl2(20 ml 3). The combined organic phase was washed with brine(20 ml 3), dried over Na2SO4, concentrated to afford yellow solid.Purification by silica gel column chromatography (PE:EA = 15:1) yielded the isoflavone amide derivatives HY-1a-HY-1f
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h;	General synthetic procedure for compounds 8-11 and 13-36 General procedure: To a stirred suspension of various carboxylic acid 4a, 4b, 6a and 8a (1.0 equiv) in CH2Cl2 (25 mL) was added oxalyl chloride (3.0 equiv) and a catalytic amount of DMF. After stirring at room temperature for 3 h, the reaction was concentrated under reduced pressure to afford a yellow oil crude acyl chloride. To a solution of methyl 2-(4-amino-2-fluorophenoxy)acetate 3a (1.0 equiv) in CH2Cl2(25 mL) was added Et3N (1.5 equiv), and this mixture was cooled to -5 °C. Subsequently, the crude acyl chloride obtained above was added in dropwise at a rate to ensure that the temperature did not exceed 0 °C. The solution was stirred for another 2 hrs at 25 °C, then washed successively with 10% HCl (2 × 25 mL), 10% NaHCO3 (2 × 25 mL) and brine (2 × 20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was then evaporated to give the impure amide which was recrystallized from ethanol to give the desired products as colorless crystals. To a solution of the obtained crystals (1.0 equiv)in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 8-11 and 13-36 as colorless crystals.
	With thionyl chloride Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h;

Reference： [1]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[2]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541]
[3]Jain; Srivastava [Journal of the Indian Chemical Society, 1990, vol. 67, # 9, p. 775 - 776]
[4]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[5]Chaurasia; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 2, p. 106 - 107]
[6]Chaurasia, Sunita; Srivastava, Savitri D. [Journal of the Indian Chemical Society, 1992, vol. 69, # 1, p. 45 - 46]
[7]Osman; Botros; Kandeel; Khalil; Abd El-Latif [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 5, p. 446 - 455]
[8]Bhatt, P.; Srivastava, S. D.; Mehta, P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 5, p. 514 - 516]
[9]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]
[10]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]
[11]Current Patent Assignee: PARK FUNDING - WO2005/97119, 2005, A2 Location in patent: Page/Page column 62
[12]Location in patent: scheme or table He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[13]Location in patent: experimental part Li, Ting; Liu, Guyue; Li, Hongcai; Yang, Xinmei; Jing, Yongkui; Zhao, Guisen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2316 - 2322]
[14]Location in patent: experimental part Han, Liang; Zhu, Qiong-Yan; Jia, Jian-Hong; Li, Yu-Jin; Gao, Jian-Rong [Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1223 - 1226]
[15]Wu, Deyan; Mei, Hanbing; Tan, Ping; Lu, Weiqiang; Zhu, Jin; Wang, Wei; Huang, Jin; Li, Jian [Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387]
[16]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]
[17]Li, Zheng; Wang, Xuekun; Xu, Xue; Yang, Jianyong; Qiu, Qianqian; Qiang, Hao; Huang, Wenlong; Qian, Hai [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 20, p. 6666 - 6672]
[18]Sheng, Xijun; Zhou, Yuan; Zhang, Shasha; Peng, Hao; He, Hongwu [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 165 - 170]
[19]Noncovich, Alain; Priest, Chad; Ung, Jane; Patron, Andrew P.; Servant, Guy; Brust, Paul; Servant, Nicole; Faber, Nathan; Liu, Hanghui; Gonsalves, Nicole S.; Ditschun, Tanya L. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 16, p. 3931 - 3938]
[20]Lei, Kang; Li, Pan; Yang, Xue-Fang; Wang, Shi-Ben; Wang, Xue-Kun; Hua, Xue-Wen; Sun, Bin; Ji, Lu-Sha; Xu, Xiao-Hua [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 37, p. 10489 - 10497]

4
[ 1643-15-8 ]
[ 13605-19-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With borohydride exchange resin In methanol for 0.5h; Ambient temperature;
	With lithium aluminium tetrahydride; diethyl ether

Reference： [1]Joshi, D. D.; Sagar, A. D.; Hilage, N. P.; Salunkhe, M. M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 12, p. 1201 - 1202]
[2]Kjeldgaard [Farmaceutisk tidende, 1956, vol. 66, p. 33,39]

5
[ 108-39-4 ]
[ 79-11-8 ]
[ 1643-15-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium hydroxide In ethanol; water for 4h; Heating;
85%	With sodium hydroxide In water at 60℃; for 7h;
57%	With potassium hydroxide In water Reflux;	4.1.3. Synthesis of Phenoxy Acetic Acid Derivatives (PAA1-PAA5) General procedure: The phenol derivative (19.2 mmol) was mixed with a solutionof potassium hydroxide (71.4 mmol, 4 g) in 8mL ofwater in a two necked round bottom flask until homogeneoussolution was produced. As the mixture began to boil, 6mL of50% w/v solution (g/ml) of chloroacetic acid was addeddrop-wise using dropping funnel placed in the side arm ofthe flask. The reaction mixture was refluxed until reactionwas completed (monitored by TLC). The solution was transferredto a beaker, cooled to room temperature and acidifiedby drop-wise addition of HCl (monitor using pH paper). Theresultant mixture was cooled in an ice bath, the crude productwas filtered and re-crystallized from boiling water.

	With sodium hydroxide Erhitzen auf dem Dampfbad;
	With alkali
	With sodium hydroxide Heating;
	With sodium hydroxide In water Heating;
	With sodium hydroxide Heating;
	With sodium hydroxide In water for 2h;
	With sodium hydroxide
	With potassium carbonate In acetone for 8h; Reflux;
	With sodium hydroxide
	With sodium hydroxide
	Stage #1: 3-methyl-phenol; chloroacetic acid With sodium hydroxide at 100℃; Stage #2: With hydrogenchloride In water
	Stage #1: 3-methyl-phenol With sodium hydroxide In water Stage #2: chloroacetic acid In water at 40 - 85℃; for 2h; Stage #3: With hydrogenchloride In water at 20℃;	4.5.1. Phenoxyacetic acids (7) General procedure: An appropriately substituted phenol (50 mmol) was added to a solution of NaOH (187.5 mmol) in 15 mL of H2O. Chloroacetic acid (85 mmol) was added slowly at to the resulting solution at 40 °C and the reaction mixture was heated to 85 °C. Stirring was continued for 2 h, the reaction was cooled to room temperature and 100 mL H2O was added. The reaction was filtered and the filtrate was acidified with concentrated HCl to pH 1-2. The brown oil fraction which formed was extracted to diethylether (2 × 50 ml). The ether fraction, in turn, was extracted with an aqueous solution of 5% Na2CO3 (2 × 37.5 ml). The combined Na2CO3 fractions were acidified to pH 1-2 with concentrated HCl and the resulting precipitate was collected by filtration and oven dried to obtain the required acids.24
	With sodium hydroxide In water	General procedure for the synthesis of aryloxy acetic/propionicacids (2a-q and 3a-q) General procedure: Equimolar quantities of 2-chloro acetic acid/3-chloro propionicacid (0.05 mol) and appropriate phenol (1a-q) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH(0.12 mol in 25 mL water) was slowly added with constant stirring.The solution was stirred for 2 h until the solution turned clear,brown or yellow and then the reaction mixture was evaporatedin a evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified byadding con. HCl. The precipitated aryloxy acetic/propionic acidwas filtered and recrystallized from water or ethanol

Reference： [1]Ramalingam, T.; Sattur, P. B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 1204 - 1207]
[2]Del Carmen Cruz, María; Tamariz, Joaquín [Tetrahedron, 2005, vol. 61, # 42, p. 10061 - 10072]
[3]Singh, Gurmeet; Bansal, Yogita; Bansal, Gulshan; Goel, Rajesh Kumar [Medicinal Chemistry, 2014, vol. 10, # 4, p. 418 - 425]
[4]Koelsch [Journal of the American Chemical Society, 1931, vol. 53, p. 304]
[5]Mameli [Gazzetta Chimica Italiana, 1926, vol. 56, p. 764] Higginbotham; Stephen [Journal of the Chemical Society, 1920, vol. 117, p. 1541] Brueckner [Angewandte Chemie, 1928, vol. 41, p. 1046][Fresenius' Zeitschrift fuer Analytische Chemie, 1928, vol. 75, p. 290]
[6]BAKER; LEE; SKINNER; MARTINEZ; TONG [Journal of medicinal and pharmaceutical chemistry, 1960, vol. 2, p. 633 - 657]
[7]Purohit; Srivastava [Journal of the Indian Chemical Society, 1991, vol. 68, # 3, p. 163 - 165]
[8]Purohit; Shah [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 5, p. 618 - 622]
[9]Shishoo, Chamanlal J.; Shirsath, Vikas S.; Rathod, Ishwarsinh S.; Yande, Vikas D. [European Journal of Medicinal Chemistry, 2000, vol. 35, # 3, p. 351 - 358]
[10]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]
[11]Location in patent: body text Khanum, Shaukath Ara; Khanum, Noor Fatima; Shashikanth [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4597 - 4601]
[12]Location in patent: scheme or table Azam, M. Afzal; Suresh, Bhojraj; Kalsi, Sandip S.; Antony, A. Shinesh [South African Journal of Chemistry, 2010, vol. 63, p. 114 - 122]
[13]Location in patent: scheme or table He, Hong-Wu; Yuan, Jun-Lin; Peng, Hao; Chen, Ting; Shen, Ping; Wan, Shu-Qing; Lee, Yanjun; Tan, Hong-Liang; He, Ya-Hui; He, Jun-Bo; Li, Yan [Journal of Agricultural and Food Chemistry, 2011, vol. 59, # 9, p. 4801 - 4813]
[14]Location in patent: scheme or table Li, Ting; Liu, Guyue; Li, Hongcai; Yang, Xinmei; Jing, Yongkui; Zhao, Guisen [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 7, p. 2316 - 2322]
[15]Location in patent: experimental part Okaecwe, Thokozile; Swanepoel, Abraham J.; Petzer, Anél; Bergh, Jacobus J.; Petzer, Jacobus P. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4336 - 4347]
[16]Joshi, Shrinivas D.; More, Uttam A.; Koli, Deepshikha; Kulkarni, Manoj S.; Nadagouda, Mallikarjuna N.; Aminabhavi, Tejraj M. [Bioorganic Chemistry, 2015, vol. 59, p. 151 - 167]

6
[ 108-30-5 ]
[ 1643-15-8 ]
[ 1222-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide; nitrobenzene
	With aluminium trichloride In nitrobenzene for 72h; Ambient temperature;

Reference： [1]Current Patent Assignee: MERCK & CO INC - BE612755, 1962, A [Chem.Abstr., 1963, vol. 59, # 12712][Chem.Abstr., 1963, vol. 59, # 12712] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]
[2]Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577]

7
[ 1643-15-8 ]
[ 121320-45-4 ]
[ 794-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide

Reference： [1]Current Patent Assignee: MERCK & CO INC - BE612755, 1962, A [Chem.Abstr., 1963, vol. 59, # 12712][Chem.Abstr., 1963, vol. 59, # 12712] Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577] Current Patent Assignee: MERCK & CO INC - US3251064, 1966, A [Chem.Abstr., 1966, vol. 65, # 8822][Chem.Abstr., 1966, vol. 65, # 8822] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]

8
[ 1643-15-8 ]
[ 75-36-5 ]
[ 1642-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide

Reference： [1]Current Patent Assignee: MERCK & CO INC - BE612755, 1962, A [Chem.Abstr., 1963, vol. 59, # 12712][Chem.Abstr., 1963, vol. 59, # 12712] Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577] Current Patent Assignee: MERCK & CO INC - US3251064, 1966, A [Chem.Abstr., 1966, vol. 65, # 8822][Chem.Abstr., 1966, vol. 65, # 8822] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]

9
[ 1643-15-8 ]
[ 141-75-3 ]
[ 1144-57-6 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide
	With aluminium trichloride In carbon disulfide

Reference： [1]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]
[2]Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]

10
[ 1643-15-8 ]
[ 79-04-9 ]
[ 1142-09-2 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide

Reference： [1]Current Patent Assignee: MERCK & CO INC - BE612755, 1962, A [Chem.Abstr., 1963, vol. 59, # 12712][Chem.Abstr., 1963, vol. 59, # 12712] Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577] Current Patent Assignee: MERCK & CO INC - US3251064, 1966, A [Chem.Abstr., 1966, vol. 65, # 8822][Chem.Abstr., 1966, vol. 65, # 8822] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]

11
[ 1643-15-8 ]
[ 4635-59-0 ]
[ 1148-02-3 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide

Reference： [1]Current Patent Assignee: MERCK & CO INC - BE639727, 1964, A [Chem.Abstr., 1965, vol. 62, # 14577][Chem.Abstr., 1965, vol. 62, # 14577] Current Patent Assignee: MERCK & CO INC - US3251064, 1966, A [Chem.Abstr., 1966, vol. 65, # 8822][Chem.Abstr., 1966, vol. 65, # 8822] Current Patent Assignee: MERCK & CO INC - US3255241, 1966, A [Chem.Abstr., 1966, vol. 65, # 5406][Chem.Abstr., 1966, vol. 65, # 5406]

12
[ 102-71-6 ]
[ 1643-15-8 ]
[ 84744-05-8 ]

Yield	Reaction Conditions	Operation in experiment
96.2%	In ethanol

Reference： [1]Voronkov, M. G.; Semenova, N. V.; Kazimirovskaya, V. B.; Kholdeeva, L. N.; Moskvitina, L. T.; et al. [Pharmaceutical Chemistry Journal, 1986, vol. 20, # 8, p. 555 - 558][Khimiko-Farmatsevticheskii Zhurnal, 1986, vol. 20, # 8, p. 952 - 956]

13
[ 1643-15-8 ]
[ 588-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium chlorate In acetic acid

Reference： [1]Eckstein, Zygmunt; Smereczynski, Krzysztof [Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 659 - 660]

14
[ 1643-15-8 ]
[ 95-54-5 ]
[ 3156-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride Heating;
	With hydrogenchloride Microwave irradiation;
	With hydrogenchloride

Reference： [1]Murray, Michael; Ryan, Adrian J.; Little, Peter J. [Journal of Medicinal Chemistry, 1982, vol. 25, # 8, p. 887 - 892]
[2]Location in patent: scheme or table Wei, Tai-Bao; Hua, Mao-Tang; Shi, Hai-Xiong; Liu, Yong; Zhang, You-Ming [Journal of Chemical Research, 2010, # 8, p. 452 - 454]
[3]Zhao, Li; Qiu, Guirong; Wu, Jiacheng; Wang, Zhiyuan; Gu, Haibin [Journal of the Chemical Society of Pakistan, 2017, vol. 39, # 4, p. 628 - 639]

15
[ 1643-15-8 ]
[ 158941-63-0 ]
3-[2-hydroxy-4-phenyl-3-(2-m-tolyloxy-acetylamino)-butyryl]-thiazolidine-4-carboxylic acid tert-butylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide

Reference： [1]Mimoto, Tsutomu; Kato, Ryohei; Takaku, Haruo; Nojima, Satoshi; Terashima, Keisuke; Misawa, Satoru; Fukazawa, Tominaga; Ueno, Takamasa; Sato, Hideharu; Shintani, Makoto; Kiso, Yoshiaki; Hayashi, Hideya [Journal of Medicinal Chemistry, 1999, vol. 42, # 10, p. 1789 - 1802]

16
[ 63051-20-7 ]
[ 1643-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In methanol
	With water; sodium hydroxide Microwave irradiation;
	With lithium hydroxide monohydrate In methanol; water for 2h; Reflux;	General Procedure for Synthesis of Substituted acetamides (4a-4hh, 4' and 4'') General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH•H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.

With lithium hydroxide In methanol; water at 50℃; for 12h;

Reference： [1]Mimoto, Tsutomu; Kato, Ryohei; Takaku, Haruo; Nojima, Satoshi; Terashima, Keisuke; Misawa, Satoru; Fukazawa, Tominaga; Ueno, Takamasa; Sato, Hideharu; Shintani, Makoto; Kiso, Yoshiaki; Hayashi, Hideya [Journal of Medicinal Chemistry, 1999, vol. 42, # 10, p. 1789 - 1802]
[2]Location in patent: scheme or table Wei, Tai-Bao; Hua, Mao-Tang; Shi, Hai-Xiong; Liu, Yong; Zhang, You-Ming [Journal of Chemical Research, 2010, # 8, p. 452 - 454]
[3]Mori, Hisashi; Wada, Ryogo; Li, Jie; Ishimoto, Tetsuya; Mizuguchi, Mineyuki; Obita, Takayuki; Gouda, Hiroaki; Hirono, Shuichi; Toyooka, Naoki [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3732 - 3735]
[4]Lei, Kang; Li, Pan; Yang, Xue-Fang; Wang, Shi-Ben; Wang, Xue-Kun; Hua, Xue-Wen; Sun, Bin; Ji, Lu-Sha; Xu, Xiao-Hua [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 37, p. 10489 - 10497]

17
[ 1643-15-8 ]
[ 36304-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In methanol for 25h; Heating;
	Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating

Reference： [1]Bhat; Bhat; Shenoy [Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 2, p. 267 - 272]
[2]Shi; Shi; Wang [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 4, p. 929 - 932]

18
[ 1643-15-8 ]
[ 2231-57-4 ]
4-amino-5-mercapto-3-(3-tolyloxymethyl)-s-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	at 180℃; for 0.25h;

Reference： [1]Ghorab; El-Sharief; Ammar; Mohamed [Phosphorus, Sulfur and Silicon and the Related Elements, 2001, vol. 173, p. 223 - 233]

19
[ 1643-15-8 ]
[ 98-09-9 ]
C₁₅H₁₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; PEG 400 In acetonitrile for 0.5h; Heating;
	With potassium carbonate for 0.0833333h;

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]
[2]Wang, Xicun; Li, Zheng; Quan, Zhengjun; Lu, Xinsheng; Gou, Ruhu [Synthetic Communications, 2003, vol. 33, # 16, p. 2891 - 2897]

20
[ 1643-15-8 ]
[ 16078-71-0 ]
1-phenyl-5-(2-m-tolyloxy-acetylamino)-1H-pyrazole-4-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With phosphorus trichloride In xylene for 3h; Heating;

Reference： [1]Abdel-Gawad, Soad M.; Ghorab; El-Sharief; El-Telbany; Abdel-Alla [Heteroatom Chemistry, 2003, vol. 14, # 6, p. 530 - 534]

21
[ 1643-15-8 ]
[ 713517-90-9 ]
5-(2,6-dichloro-benzyl)-9b-phenyl-1-m-tolyloxy-5,9b-dihydro-1H-2a,5-diaza-benzo[a]cyclobuta[c]cycloheptene-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Bolli, Martin H.; Marfurt, Judith; Grisostomi, Corinna; Boss, Christoph; Binkert, Christoph; Hess, Patrick; Treiber, Alexander; Thorin, Eric; Morrison, Keith; Buchmann, Stephan; Bur, Daniel; Ramuz, Henri; Clozel, Martine; Fischli, Walter; Weller, Thomas [Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2776 - 2795]

22
[ 3926-62-3 ]
[ 108-39-4 ]
[ 1643-15-8 ]

Yield	Reaction Conditions	Operation in experiment
75.7%	With sodium hydroxide In ethanol; water for 1h; Reflux;
	With sodium hydroxide In water at 60℃; for 8h;

Reference： [1]Location in patent: experimental part Han, Liang; Zhu, Qiong-Yan; Jia, Jian-Hong; Li, Yu-Jin; Gao, Jian-Rong [Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1223 - 1226]
[2]Cruz, María Del Carmen; Tamariz, Joaquín [Tetrahedron Letters, 2004, vol. 45, # 11, p. 2377 - 2380]

23
[ 66047-01-6 ]
[ 1643-15-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: ethyl 3-methylphenoxyacetate With sodium hydroxide In tetrahydrofuran for 2h; Reflux; Stage #2: With hydrogenchloride In water
	With potassium hydroxide In water for 1h; Heating;
	With sodium hydroxide; water In methanol

	With potassium hydroxide In ethanol; water at 20℃; for 1.5h;	General procedure for the synthesis of 5a-f General procedure: A mixture of phenols (0.3 mmol), acetone (10 ml), dimethylformamide(10 ml), ethyl chloroacetate (2.5 ml, 0.26 mmol), potassiumcarbonate (2 g) and potassium iodide (0.15 g) was heated at75 C for 12 h. Afterwards, the solid was filtered and the solventof the filtrate was removed in vacuo. The colorless liquid (4a-f)obtained was dissolved in ethanol (20 ml). A solution of potassiumhydroxide (7.2%, 5 ml) was added and stirred at room temperaturefor 1.5 h. The mixture was poured into hydrochloric acid (1 mol/L)and a white precipitate was formed. Purification by recrystallizationfrom methanol afforded the corresponding aryloxyl acid (5a-f)
	With sodium hydroxide In methanol at 20℃; for 0.166667h;

Reference： [1]Ozcan, Sevil; Kazi, Aslamuzzaman; Marsilio, Frank; Fang, Bin; Guida, Wayne C.; Koomen, John; Lawrence, Harshani R.; Sebti, Saïd M. [Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3783 - 3805]
[2]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]
[3]Location in patent: scheme or table Hidaka, Koushi; Kimura, Tooru; Ruben, Adam J.; Uemura, Tsuyoshi; Kamiya, Mami; Kiso, Aiko; Okamoto, Tetsuya; Tsuchiya, Yumi; Hayashi, Yoshio; Freire, Ernesto; Kiso, Yoshiaki [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 23, p. 10049 - 10060]
[4]Wang, Wenbin; He, Yi; Xu, Pei; You, Qidong; Xiao, Hong; Xiang, Hua [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4428 - 4433]
[5]De Souza, Mariana L.; De Oliveira Rezende Junior, Celso; Ferreira, Rafaela S.; Espinoza Chávez, Rocio Marisol; Ferreira, Leonardo L. G.; Slafer, Brian W.; Magalhães, Luma G.; Krogh, Renata; Oliva, Glaucius; Cruz, Fabio Cardoso; Dias, Luiz Carlos; Andricopulo, Adriano D. [Journal of Chemical Information and Modeling, 2020, vol. 60, # 2, p. 1028 - 1041]

24
[ 1643-15-8 ]
[ 79-19-6 ]
[ 84138-76-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: 2-(m-tolyloxy)acetic acid; thiosemicarbazide With trichlorophosphate for 0.5h; Reflux; Stage #2: With water for 4h; Reflux;
	With poly(ethylene glycol)-supported dichlorophosphate at 120℃; microwave irradiation;
	With trichlorophosphate at 100℃; for 4h;

Stage #1: 2-(m-tolyloxy)acetic acid; thiosemicarbazide With trichlorophosphate at 75℃; for 0.5h; Stage #2: In water for 4h; Reflux;

General procedure for the preparation of 2-((phenoxy orsubstituted phenoxy)methyl/ethyl)-1,3,4-thiadiazol-5-amines (4a-qand 5a-q) General procedure: A mixture of benzoic acid (50 mmol), N-aminothiourea(50 mmol) and POCl3 (13 mL) was heated at 75 C for 0.5 h. Themixture was cooled to which water (10 mL) was added and thereaction mixture was refluxed for 4 h. The mixture was cooled and pH was adjusted to 8.0 by adding 50% sodium hydroxide solution.The separated solid was filtered and recrystallized from ethanolto give desired compounds.

Reference： [1]Location in patent: experimental part Azam, M. Afzal; Suresh, Bhojraj; Kalsi, Sandip S.; Antony, A. Shinesh [South African Journal of Chemistry, 2010, vol. 63, p. 114 - 122]
[2]Li, Zheng; Yu, Jin-Lan; Yang, Jing-Ya; Zhu, Wei; Zhao, Yan-Long; Xing, Yu-Lin; Wang, Xi-Cun [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 1, p. 183 - 190]
[3]Location in patent: scheme or table Wang, Xi Cun; Ding, Xiao Mei; Wang, Sheng Qing; Chen, Xue Fei; Quan, Zheng Jun [Chinese Chemical Letters, 2010, vol. 21, # 3, p. 301 - 304]
[4]Joshi, Shrinivas D.; More, Uttam A.; Koli, Deepshikha; Kulkarni, Manoj S.; Nadagouda, Mallikarjuna N.; Aminabhavi, Tejraj M. [Bioorganic Chemistry, 2015, vol. 59, p. 151 - 167]

25
[ 1643-15-8 ]
3-(4-chlorophenyl)-4-amino-5-mercapto-[1,2,4]-triazole [ No CAS ]
C₂₁H₁₅N₄O₂SCl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With trichlorophosphate microwave irradiation;

Reference： [1]Wang, Xi-Cun; Liu, Juan [Synthetic Communications, 2007, vol. 37, # 8, p. 1339 - 1346]

26
[ 1643-15-8 ]
[ 79-03-8 ]
[ 1006585-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In carbon disulfide

Reference： [1]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]

27
[ 1643-15-8 ]
C₁₃H₁₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AlCl₃ / CS₂ 2: 27.3 percent / K₂CO₃

Reference： [1]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]

28
[ 1643-15-8 ]
[ 1148-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: AlCl₃ / CS₂ 2: 33.3 percent / K₂CO₃

Reference： [1]Zhao, Guisen; Liu, Chuan; Wang, Rui; Song, Dandan; Wang, Xiaobing; Lou, Hongxiang; Jing, Yongkui [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 7, p. 2701 - 2707]

29
[ 1643-15-8 ]
3-cyano-2,4-dimethyl-benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / hexane / Heating 2: 92 percent / CH₂Cl₂ / 12 h / 20 °C 3: 70 percent / 0.12 h / microwave irradiation

Reference： [1]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]

30
[ 1643-15-8 ]
[ 826990-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / hexane / Heating 2: 92 percent / CH₂Cl₂ / 12 h / 20 °C

Reference： [1]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]

31
[ 108-39-4 ]
[ 1643-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / acetone / 3 h / Heating 2: potassium hydroxide / H₂O / 1 h / Heating

Reference： [1]RamaRao; Venkat Reddy; Maitraie; Ravikanth; Yadla; Narsaiah; Shanthan Rao [Tetrahedron, 2004, vol. 60, # 52, p. 12231 - 12237]

32
[ 1643-15-8 ]
rac-(SR)-[(5SR)-1-(2,6-dichlorobenzyl)-2-oxo-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-5-yl]-m-tolyloxyacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 99 percent / Et₃N; bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 0 - 20 °C 2: 82 percent / aq. LiOH / tetrahydrofuran; methanol / 45 - 60 °C

Reference： [1]Bolli, Martin H.; Marfurt, Judith; Grisostomi, Corinna; Boss, Christoph; Binkert, Christoph; Hess, Patrick; Treiber, Alexander; Thorin, Eric; Morrison, Keith; Buchmann, Stephan; Bur, Daniel; Ramuz, Henri; Clozel, Martine; Fischli, Walter; Weller, Thomas [Journal of Medicinal Chemistry, 2004, vol. 47, # 11, p. 2776 - 2795]

33
[ 1643-15-8 ]
5-amino-1-phenyl-6-m-tolyloxymethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 62 percent / phosphorus trichloride / xylene / 3 h / Heating 2: 84 percent / hydrazine hydrate / butan-1-ol / Heating

Reference： [1]Abdel-Gawad, Soad M.; Ghorab; El-Sharief; El-Telbany; Abdel-Alla [Heteroatom Chemistry, 2003, vol. 14, # 6, p. 530 - 534]

34
[ 1643-15-8 ]
2-(3-methylphenyloxyacetylamido)-5-phenyloxymethyl-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]

35
[ 1643-15-8 ]
2-(3-methylphenyloxyacetylamido)-5-(4-methoxyphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]

36
[ 1643-15-8 ]
2-(3-methylphenyloxyacetylamido)-5-(2-methylphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]

37
[ 1643-15-8 ]
2-(3-methylphenyloxyacetylamido)-5-(4-methylphenyloxymethyl)-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]

38
[ 1643-15-8 ]
2-(3-methylphenyloxyacetylamido)-5-(1-naphthyloxymethyl)-1,3,4-thiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃; PEG 400 / acetonitrile / 0.5 h / Heating 2: acetonitrile / 1 h / Heating

Reference： [1]Wang, Xicun; Li, Zheng; Ji, Dong; Da, Yuxia [Synthetic Communications, 2002, vol. 32, # 7, p. 1091 - 1096]

39
[ 1643-15-8 ]
3-(3-tolyloxymethyl)-6,11-dioxonaphtho[5,6:2,3][1,3,4]thiadiazino[2,3-c]-s-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 75 percent / 0.25 h / 180 °C 2: 76 percent / Et₃N / dimethylformamide / 12 h / Heating

Reference： [1]Ghorab; El-Sharief; Ammar; Mohamed [Phosphorus, Sulfur and Silicon and the Related Elements, 2001, vol. 173, p. 223 - 233]

40
[ 1643-15-8 ]
[ 372164-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating 3: aq. HCl / 4 h / Heating 4: 85.3 percent / 8 percent aq. NaOH / 4 h / 95 °C

Reference： [1]Shi; Shi; Wang [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 4, p. 929 - 932]

41
[ 1643-15-8 ]
[ 372164-11-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: p-toluenesulfonic acid / 5 h / Heating 2: hydrazine hydrate / ethanol / 3 h / Heating 3: aq. HCl / 4 h / Heating

Reference： [1]Shi; Shi; Wang [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 4, p. 929 - 932]

42
[ 1643-15-8 ]
3-(3-methylphenoxymethyl)-4-N-[pyrazin-2-carboxamido]-1,2,4-triazole-5-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydrazine hydrate / conc. H₂SO₄ / methanol / 25 h / Heating 2: KOH / ethanol / 2 h 3: 68 percent / 6 h / 160 - 180 °C / Heating

Reference： [1]Bhat; Bhat; Shenoy [Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 2, p. 267 - 272]

43
[ 1643-15-8 ]
4-N-(3-methylphenoxymethyl carboxamido)-3-(pyrazin-2-yl)-1,2,4-triazole-5-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrazine hydrate / conc. H₂SO₄ / methanol / 25 h / Heating 2: 82 percent / 8 h / 160 - 180 °C / Heating

Reference： [1]Bhat; Bhat; Shenoy [Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 2, p. 267 - 272]

44
[ 1643-15-8 ]
C₁₀H₁₁N₂O₂S₂^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrazine hydrate / conc. H₂SO₄ / methanol / 25 h / Heating 2: KOH / ethanol / 2 h

Reference： [1]Bhat; Bhat; Shenoy [Journal of Pharmacy and Pharmacology, 2001, vol. 53, # 2, p. 267 - 272]

45
[ 1643-15-8 ]
[ 109395-46-2 ]