[ CAS No. 14316-14-4 ]

Name: 14316-14-4|N-(2-Hydroxyethyl)-4-methylbenzenesulfonamide|95+%
Brand: Ambeed
SKU: A198857
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Quality Control of [ 14316-14-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 14316-14-4 ]

SDS

Alternatived Products of [ 14316-14-4 ]

Product Details of [ 14316-14-4 ]

CAS No. :	14316-14-4	MDL No. :	MFCD00464177
Formula :	C₉H₁₃NO₃S	Boiling Point :	380.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	215.27 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 14316-14-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.27
TPSA :	74.78 Å²

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) :	-7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.41
Log Po/w (XLOGP3) :	0.57
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	0.43
Log Po/w (SILICOS-IT) :	0.55
Consensus Log Po/w :	0.86

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.59
Solubility :	5.57 mg/ml ; 0.0259 mol/l
Class :	Very soluble
Log S (Ali) :	-1.71
Solubility :	4.17 mg/ml ; 0.0194 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.0
Solubility :	0.214 mg/ml ; 0.000993 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.16

Safety of [ 14316-14-4 ]

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 [ 14316-14-4 ]

* 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 [ 14316-14-4 ]

[ 14316-14-4 ] Synthesis Path-Downstream 1~31

1
[ 141-43-5 ]
[ 98-59-9 ]
[ 14316-14-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;
99%	With triethylamine In dichloromethane at 0 - 20℃; for 24h;
96%	With pyridine at 5 - 20℃;

94%	With triethylamine In dichloromethane at 0 - 20℃; for 2h;
91%	With zinc oxide-nanoparticle at 50℃; Neat (no solvent); chemoselective reaction;
90%	With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h;
90%	With tetrabutylammomium bromide; sodium hydroxide In benzene at 0 - 20℃; for 8h;
89%	With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h; stereoselective reaction;
89%	With triethylamine In dichloromethane at 0 - 20℃;
85%	With triethylamine In dichloromethane at 20℃;
83%	With triethylamine In dichloromethane at 0 - 20℃; for 18h;
81%	With triethylamine In dichloromethane at 0 - 25℃; for 0.333333h;
70%	In toluene Heating;
70%	With triethylamine In dichloromethane at 0 - 20℃;
70%	With triethylamine In dichloromethane at 20℃; for 18h; Schlenk technique; Cooling with ice;
68%	With triethylamine In dichloromethane at 0℃; for 8h;
68%	With triethylamine In dichloromethane at 20℃; for 17h; Sealed tube; Inert atmosphere;
61%	With triethylamine In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere; Cooling with ice;
43%	With dmap; triethylamine In dichloromethane at 0 - 20℃;	General procedure for the preparation of N-protected aminoalcohols General procedure: To a solution of aminoalcohol (10 mmol), DMAP (1 mmol) and triethylamine (20 mmol) in CH2Cl2(2.0 M) at 0 °C, a solution of the suitable sulfonyl chloride was added dropwise (10.5 mmol) inCH2Cl2 (50 mL) and the resulting mixture was stirred at room temperature overnight. The mixturewas washed with water (3 x 50 mL) and brine (1 x 50 mL), then dried over Na2SO4, andconcentrated at reduced pressure. The crude product was purified by silica gel columnchromatography to afford the corresponding protected aminoalcohol.
	With pyridine
	With sodium hydroxide
	With sodium hydroxide In benzene
	In N,N-dimethyl-formamide
	With hydrogenchloride In dichloromethane; water	a I. a) 100 g of p-toluenesulfonyl chloride are slowly added over 1.5 hour to 80 ml of ethanolamine while cooling with ice. The reaction mixture is then heated to 120° C. and is then held at this temperature for 3 hours. After cooling to 70° C., a mixture of 60 ml of concentration HCl and 300 ml of water is added. After stirring for 10 min, 300 ml of methylene chloride are added, and the organic phase is separated and dried with MgSO4. After stripping off the solvent on the rotary evaporator, 111.6 g of a slightly yellowish solid [N-(2-hydroxyethyl)-p-toluenesulfonamide] are obtained. The product can be used in the next step without further purification.
	With sodium hydroxide; tetrabutylammomium bromide In water; benzene
	With triethylamine In tetrahydrofuran; water at 0 - 20℃;
	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
	With triethylamine In dichloromethane at 20℃; for 16h;
	With triethylamine In dichloromethane at 20℃;
	With triethylamine In chloroform at 20℃; for 16h;
	With triethylamine In dichloromethane
	With triethylamine In dichloromethane at 20℃;
	With silica gel for 0.5h; Inert atmosphere;
	With triethylamine In dichloromethane at 20℃;
	With triethylamine In dichloromethane at 20℃;
	With silica gel Inert atmosphere;
	In ethyl acetate at 20℃; for 2h;	Typical procedure for the synthesis of starting materials General procedure: Tosylation: To a solution of p-toluenesulfonyl chloride (5 mmol, 1.0 equiv) in EtOAc (10 mL) was added proper alkanolamine (10 mmol, 2.0 equiv). The reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was filtered through silica and washed with EtOAc. The residue was concentrated to give products, which were used to next step without further purification.
2 g	With triethylamine In dichloromethane at 20℃; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
	With triethylamine In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
	With dmap; triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;

Reference： [1]Law, Katherine R.; McErlean, Christopher S. P. [Chemistry - A European Journal, 2013, vol. 19, # 47, p. 15852 - 15855]
[2]Venning, Alexander R. O.; Kwiatkowski, Megan R.; Roque Peña, Joan E.; Lainhart, Brendan C.; Guruparan, Akil A.; Alexanian, Erik J. [Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11595 - 11600]
[3]Li, Long; Zhou, Bo; Wang, Yong-Heng; Shu, Chao; Pan, Yi-Fei; Lu, Xin; Ye, Long-Wu [Angewandte Chemie - International Edition, 2015, vol. 54, # 28, p. 8245 - 8249][Angew. Chem., 2015, vol. 54, p. 8245 - 8249,4]
[4]Cabrera-Lobera, Natalia; Quirós, M. Teresa; Buñuel, Elena; Cárdenas, Diego J. [Chemistry - A European Journal, 2019, vol. 25, # 64, p. 14512 - 14516]
[5]Location in patent: scheme or table Tamaddon, Fatemeh; Sabeti, Mohammad Reza; Jafari, Abbas Ali; Tirgir, Farhang; Keshavarz, Elham [Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45]
[6]Location in patent: scheme or table Jayagobi, Mathesan; Raghunathan, Raghavachary [Tetrahedron Letters, 2009, vol. 50, # 49, p. 6886 - 6890]
[7]Location in patent: scheme or table Jayagobi, Mathesan; Poornachandran, Mahalingam; Raghunathan, Raghavachary [Tetrahedron Letters, 2009, vol. 50, # 6, p. 648 - 650]
[8]Balaji, Pandur Venkatesan; Chandrasekaran, Srinivasan [Chemical Communications, 2013, vol. 50, # 1, p. 70 - 72]
[9]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2018/137573, 2018, A1 Location in patent: Page/Page column 106
[10]Fukudome, Yasuhiro; Naito, Hiroyuki; Hata, Takeshi; Urabe, Hirokazu [Journal of the American Chemical Society, 2008, vol. 130, # 6, p. 1820 - 1821]
[11]Wen, Ke; Wu, Zhengxing; Chen, Buyun; Chen, Jianzhong; Zhang, Wanbin [Organic and Biomolecular Chemistry, 2018, vol. 16, # 31, p. 5618 - 5625]
[12]Engl, Sebastian; Reiser, Oliver [Organic Letters, 2021, vol. 23, # 14, p. 5581 - 5586]
[13]Gomez, Jose A.; Trujillo, Maria A.; Campos, Joaquin; Gallo, Miguel A.; Espinosa, Antonio [Tetrahedron, 1998, vol. 54, # 43, p. 13295 - 13312]
[14]Elliott, Luke D.; Wrigglesworth, Joe W.; Cox, Brian; Lloyd-Jones, Guy C.; Booker-Milburn, Kevin I. [Organic Letters, 2011, vol. 13, # 4, p. 728 - 731]
[15]Chao, Tzu-Hsuan; Chen, Wei-Chen; Cheng, Chien-Hong; Cheng, Lin-Chieh; Cheng, Mu-Jeng; Santhoshkumar, Rajagopal [European Journal of Organic Chemistry, 2020, vol. 2020, # 14, p. 2116 - 2129]
[16]Gandon, Lucile A.; Russell, Alexander G.; Gueveli, Tatyana; Brodwolf, Angela E.; Kariuki, Benson M.; Spencer, Neil; Snaith, John S. [Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5198 - 5207]
[17]Braga, Felipe C.; Gallou, Fabrice; Lee, Nicholas R.; Lippincott, Daniel J.; Lipshutz, Bruce H.; Moghadam, Farbod A.; Zhu, Bingchun [Organic Letters, 2020]
[18]Johnson, Renjith P.; Jeong, Young-Il; John, Johnson V.; Chung, Chung-Wook; Kang, Dae Hwan; Selvaraj, Manickam; Suh, Hongsuk; Kim, Il [Biomacromolecules, 2013, vol. 14, # 5, p. 1434 - 1443]
[19]Gazzola, Silvia; Beccalli, Egle M.; Borelli, Tea; Castellano, Carlo; Diamante, Daria; Broggini, Gianluigi [Synlett, 2018, vol. 29, # 4, p. 503 - 508]
[20]Slotta; Behnisch [Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 135, p. 225,232, 233]
[21]Linnell; Smith [Quarterly Journal of Pharmacy and Pharmacology, 1948, vol. 21, p. 121,124]
[22]Augstein,J. et al. [Journal of Medicinal Chemistry, 1965, vol. 8, p. 356 - 367] Slotta; Behnisch [Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2> 135, p. 225,232, 233]
[23]Sato, Yoshihiro; Saito, Nozomi; Mori, Miwako [Tetrahedron, 1998, vol. 54, # 7, p. 1153 - 1168]
[24]Kondo, Shin-Ichi; Suzuki, Takashi; Yano, Yumihiko [Tetrahedron Letters, 2002, vol. 43, # 39, p. 7059 - 7061]
[25]Current Patent Assignee: MERCK KGAA - US5442087, 1995, A
[26]Poornachandran, Mahalingam; Raghunathan, Raghavachary [Tetrahedron, 2008, vol. 64, # 27, p. 6461 - 6474]
[27]Zhao, Yu-Jun; Loh, Teck-Peng [Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 10024 - 10029]
[28]Huang, Jianhui; Moore, Stephen P.; O'Brien, Peter; Whitwood, Adrian C.; Gilday, John [Organic and Biomolecular Chemistry, 2009, vol. 7, # 2, p. 335 - 345]
[29]Bandini, Marco; Monari, Magda; Romaniello, Alessandro; Tragni, Michele [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14272 - 14277]
[30]Liu, Hui; Qiao, Zongjun; Jiang, Xuefeng [Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7274 - 7277]
[31]Sequeira, Fatima C.; Chemler, Sherry R. [Organic Letters, 2012, vol. 14, # 17, p. 4482 - 4485]
[32]Dwivedi, Vikas; Hari Babu, Madala; Kant, Ruchir; Sridhar Reddy, Maddi [Chemical Communications, 2015, vol. 51, # 81, p. 14996 - 14999]
[33]Ghosh, Priya; Deka, Manash J.; Saikia, Anil K. [Tetrahedron, 2016, vol. 72, # 5, p. 690 - 698]
[34]Hwang, Joon Young; Baek, Jong Hwa; Shin, Tae Il; Shin, Jung Ha; Oh, Jae Won; Kim, Kwang Pyo; You, Youngmin; Kang, Eun Joo [Organic Letters, 2016, vol. 18, # 19, p. 4900 - 4903]
[35]Dong, Xu; Han, Ying; Yan, Fachao; Liu, Qing; Wang, Ping; Chen, Kexun; Li, Yueyun; Zhao, Zengdian; Dong, Yunhui; Liu, Hui [Organic Letters, 2016, vol. 18, # 15, p. 3774 - 3777]
[36]Dong, Xu; Cui, Jie; Song, Jian; Han, Ying; Liu, Qing; Dong, Yunhui; Liu, Hui [Chemical Communications, 2017, vol. 53, # 36, p. 4903 - 4906] Ban, Yong-Liang; Dai, Jian-Ling; Jin, Xiao-Ling; Zhang, Qing-Bao; Liu, Qiang [Chemical Communications, 2019, vol. 55, # 65, p. 9701 - 9704]
[37]Kuo, Jonathan L.; Lorenc, Chris; Abuyuan, Janine M.; Norton, Jack R. [Journal of the American Chemical Society, 2018, vol. 140, # 13, p. 4512 - 4516]
[38]Hwang, Joon Young; Shin, Jung Ha; Seong, Eun Young; Kang, Eun Joo [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 695 - 698]
[39]Aubineau, Thomas; Cossy, Janine [Organic Letters, 2018, vol. 20, # 23, p. 7419 - 7423]
[40]González, Leticia; Maryasin, Boris; Maulide, Nuno; Mishevska, Magdalena; Teskey, Christopher J.; Völkl, Martin; Zawodny, Wojciech [Angewandte Chemie - International Edition, 2020, vol. 59, # 47, p. 20935 - 20939][Angew. Chem., 2020, vol. 132, # 47, p. 21121 - 21125,5]
[41]Zhou, Pan; Li, Xinxuan; Wang, Dong; Xu, Tao [Organic Letters, 2021, vol. 23, # 12, p. 4683 - 4687]
[42]Giofrè, Sabrina; Molteni, Letizia; Nava, Donatella; Lo Presti, Leonardo; Beccalli, Egle Maria [Angewandte Chemie - International Edition, 2021, vol. 60, # 40, p. 21723 - 21727][Angew. Chem., 2021, vol. 133, # 40, p. 21891 - 21895]
[43]Berhane, Ilyas A.; Burde, Ameya S.; Chemler, Sherry R.; Kennedy-Ellis, Jonathan J.; Zurek, Eva [Chemical Communications, 2021, vol. 57, # 78, p. 10099 - 10102]

3
[ 14316-14-4 ]
[ 4556-90-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 25℃; for 24h;
	With phosphorus tribromide
	With phosphorus tribromide In 1,2-dichloro-ethane

Reference： [1]Boddy, Alexander J.; Affron, Dominic P.; Cordier, Christopher J.; Rivers, Emma L.; Spivey, Alan C.; Bull, James A. [Angewandte Chemie - International Edition, 2019, vol. 58, # 5, p. 1458 - 1462][Angew. Chem., 2019, vol. 131, # 5, p. 1472 - 1476,5]
[2]Zaoral,M. et al. [Collection of Czechoslovak Chemical Communications, 1967, vol. 32, # 2, p. 843 - 853]
[3]Augstein,J. et al. [Journal of Medicinal Chemistry, 1965, vol. 8, p. 356 - 367]

4
[ 14316-14-4 ]
[ 111-44-4 ]
[ 50977-94-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In N,N-dimethyl-formamide
65%	With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 24h;
	(i) KOtBu, (ii) /BRN= 605317/; Multistep reaction;

Reference： [1]Dietrich, B.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. [Journal of the American Chemical Society, 1981, vol. 103, # 5, p. 1282 - 1283]
[2]Dietrich, Bernard; Hosseini, Mir Wais; Lehn, Jean-Marie; Sessions, Richard B. [Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1262 - 1278]
[3]King,A.P.; Krespan,C.G. [Journal of Organic Chemistry, 1974, vol. 39, p. 1315 - 1316]

5
[ 29981-92-8 ]
[ 141-43-5 ]
[ 14316-14-4 ]
[ 35487-17-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; tetramethlyammonium chloride In ethanol at 25℃; μ=0.16 M;

Reference： [1]Monjoint, P.; Ruasse, M. F. [Bulletin de la Societe Chimique de France, 1988, # 2, p. 356 - 360]

6
[ 141-43-5 ]
[ 2232-08-8 ]
[ 288-32-4 ]
[ 14316-14-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1988,p. 356 - 360

7
[ 14316-14-4 ]
[ 18162-48-6 ]
[ 202974-92-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With 1H-imidazole In dichloromethane at 20℃; for 22h; Inert atmosphere;
90%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h;
84%	With 1H-imidazole In dichloromethane at 25℃; for 22h;

72%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	General procedure for the preparation of O-(tert-butyldimethylsilyl)-N-protectedaminoalcohol General procedure: A solution of N-protected aminoalcohol (10 mmol), tert-butyldimethylsilyl chloride (20 mmol) andimidazole (20 mmol) in DMF (0.2 M) was stirred at room temperature overnight. The reaction wastaken with brine (40 mL), extracted with Et2O (3 x 40 mL), dried over Na2SO4 and concentrated atreduced pressure. The crude product was purified by silica gel column chromatography to affordthe corresponding O-(tert-butyldimethylsilyl)-N-protected aminoalcohol.3
	With 1H-imidazole In N,N-dimethyl-formamide Yield given;
	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;
	With 1H-imidazole In dichloromethane at 0℃; for 12h; Inert atmosphere;

Reference： [1]Law, Katherine R.; McErlean, Christopher S. P. [Chemistry - A European Journal, 2013, vol. 19, # 47, p. 15852 - 15855]
[2]Gandon, Lucile A.; Russell, Alexander G.; Gueveli, Tatyana; Brodwolf, Angela E.; Kariuki, Benson M.; Spencer, Neil; Snaith, John S. [Journal of Organic Chemistry, 2006, vol. 71, # 14, p. 5198 - 5207]
[3]Engl, Sebastian; Reiser, Oliver [Organic Letters, 2021, vol. 23, # 14, p. 5581 - 5586]
[4]Gazzola, Silvia; Beccalli, Egle M.; Borelli, Tea; Castellano, Carlo; Diamante, Daria; Broggini, Gianluigi [Synlett, 2018, vol. 29, # 4, p. 503 - 508]
[5]Sato, Yoshihiro; Saito, Nozomi; Mori, Miwako [Tetrahedron, 1998, vol. 54, # 7, p. 1153 - 1168]
[6]Bandini, Marco; Monari, Magda; Romaniello, Alessandro; Tragni, Michele [Chemistry - A European Journal, 2010, vol. 16, # 48, p. 14272 - 14277]
[7]Hwang, Joon Young; Baek, Jong Hwa; Shin, Tae Il; Shin, Jung Ha; Oh, Jae Won; Kim, Kwang Pyo; You, Youngmin; Kang, Eun Joo [Organic Letters, 2016, vol. 18, # 19, p. 4900 - 4903]

8
[ 7299-55-0 ]
[ 14316-14-4 ]
N-(p-toluenesulfonyl)-2-acetylmethylmorpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triphenylphosphine In acetonitrile at 80℃; for 24h;

Reference： [1]Lu, Cheng; Lu, Xiyan [Organic Letters, 2002, vol. 4, # 26, p. 4677 - 4679]

9
[ 14316-14-4 ]
[ 104662-01-3 ]
N-(p-toluenesulfonyl)-2-cyclohexanoylmethylmorpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With triphenylphosphine In acetonitrile at 80℃; for 24h;

Reference： [1]Lu, Cheng; Lu, Xiyan [Organic Letters, 2002, vol. 4, # 26, p. 4677 - 4679]

10
[ 14316-14-4 ]
[ 64819-94-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 65 percent / K₂CO₃ / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C
	Multi-step reaction with 3 steps 1: 65 percent / K₂CO₃ / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction

Reference： [1]Dietrich, Bernard; Hosseini, Mir Wais; Lehn, Jean-Marie; Sessions, Richard B. [Helvetica Chimica Acta, 1983, vol. 66, # 4, p. 1262 - 1278]
[2]Dietrich, B.; Hosseini, M. W.; Lehn, J. M.; Sessions, R. B. [Journal of the American Chemical Society, 1981, vol. 103, # 5, p. 1282 - 1283]

11
[ 14316-14-4 ]
[ 76980-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 65 percent / K₂CO₃ / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H₂O; diethyl ether / 12 h 5: 1.) sodium / 1.) EtOH, 60 deg C, 30 min; 2.) DMF, 100 deg C, 1 h
	Multi-step reaction with 5 steps 1: 65 percent / K₂CO₃ / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H₂O; diethyl ether 5: 1.) NaH / 1) DMF; 2) DMF

12
[ 14316-14-4 ]
[ 76980-40-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 65 percent / K₂CO₃ / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C 4: 57 percent / NaOH / H₂O; diethyl ether / 12 h
	Multi-step reaction with 4 steps 1: 65 percent / K₂CO₃ / dimethylformamide 2: 95 percent / pyridine 3: 82 percent / Gabriel reaction 4: 57 percent / H₂O; diethyl ether

13
[ 14316-14-4 ]
[ 76980-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 65 percent / K₂CO₃ / dimethylformamide / 24 h / 70 °C 2: 93 percent / pyridine / 0 °C
	Multi-step reaction with 2 steps 1: 65 percent / K₂CO₃ / dimethylformamide 2: 95 percent / pyridine

14
[ 38761-67-0 ]
[ 14316-14-4 ]
[ 1008757-13-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium phosphate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 130℃; for 21h;

Reference： [1]Fukudome, Yasuhiro; Naito, Hiroyuki; Hata, Takeshi; Urabe, Hirokazu [Journal of the American Chemical Society, 2008, vol. 130, # 6, p. 1820 - 1821]

15
[ 1020203-56-8 ]
[ 14316-14-4 ]
[ 1020203-73-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium phosphate In N,N-dimethyl-formamide at 110℃; for 3h;

Reference： [1]Naito, Hiroyuki; Hata, Takeshi; Urabe, Hirokazu [Tetrahedron Letters, 2008, vol. 49, # 14, p. 2298 - 2301]

16
[ 14316-14-4 ]
[ 106-95-6 ]
[ 869275-29-6 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate In acetonitrile for 0.166667h; Reflux;
	With potassium carbonate In acetone
5.5 g	Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 16h;

	With potassium carbonate In acetone Reflux;
	With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere;
	With potassium carbonate In acetone for 2h; Reflux;
	With potassium carbonate; potassium iodide In acetone for 16h; Inert atmosphere; Reflux;
	Stage #1: N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Reference： [1]Giofrè, Sabrina; Molteni, Letizia; Nava, Donatella; Lo Presti, Leonardo; Beccalli, Egle Maria [Angewandte Chemie - International Edition, 2021, vol. 60, # 40, p. 21723 - 21727][Angew. Chem., 2021, vol. 133, # 40, p. 21891 - 21895]
[2]Poornachandran, Mahalingam; Raghunathan, Raghavachary [Tetrahedron, 2008, vol. 64, # 27, p. 6461 - 6474]
[3]Sequeira, Fatima C.; Chemler, Sherry R. [Organic Letters, 2012, vol. 14, # 17, p. 4482 - 4485]
[4]Ghosh, Priya; Deka, Manash J.; Saikia, Anil K. [Tetrahedron, 2016, vol. 72, # 5, p. 690 - 698]
[5]Hwang, Joon Young; Baek, Jong Hwa; Shin, Tae Il; Shin, Jung Ha; Oh, Jae Won; Kim, Kwang Pyo; You, Youngmin; Kang, Eun Joo [Organic Letters, 2016, vol. 18, # 19, p. 4900 - 4903]
[6]Ban, Yong-Liang; Dai, Jian-Ling; Jin, Xiao-Ling; Zhang, Qing-Bao; Liu, Qiang [Chemical Communications, 2019, vol. 55, # 65, p. 9701 - 9704]
[7]Zhou, Pan; Li, Xinxuan; Wang, Dong; Xu, Tao [Organic Letters, 2021, vol. 23, # 12, p. 4683 - 4687]
[8]Berhane, Ilyas A.; Burde, Ameya S.; Chemler, Sherry R.; Kennedy-Ellis, Jonathan J.; Zurek, Eva [Chemical Communications, 2021, vol. 57, # 78, p. 10099 - 10102]

17
[ 1125-88-8 ]
[ 14316-14-4 ]
[ 70509-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20 - 70℃;

Reference： [1]Zhao, Yu-Jun; Loh, Teck-Peng [Journal of the American Chemical Society, 2008, vol. 130, # 30, p. 10024 - 10029]

18
[ 14316-14-4 ]
[ 932-87-6 ]
[ 1160723-39-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
89%	With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;
56%	With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine

With iron(III) chloride hexahydrate; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 90℃; for 12h;

Reference： [1]Yao, Bangben; Liang, Zunjun; Niu, Tianmin; Zhang, Yuhong [Journal of Organic Chemistry, 2009, vol. 74, # 12, p. 4630 - 4633]
[2]Ao, Chaoqun; Yang, Xiaohan; Jia, Shikun; Xu, Xinfang; Yuan, Yanqiu; Zhang, Dan; Hu, Wenhao [Journal of Organic Chemistry, 2019, vol. 84, # 23, p. 15331 - 15342]
[3]Li, Long; Zhou, Bo; Wang, Yong-Heng; Shu, Chao; Pan, Yi-Fei; Lu, Xin; Ye, Long-Wu [Angewandte Chemie - International Edition, 2015, vol. 54, # 28, p. 8245 - 8249][Angew. Chem., 2015, vol. 54, p. 8245 - 8249,4]
[4]Dwivedi, Vikas; Hari Babu, Madala; Kant, Ruchir; Sridhar Reddy, Maddi [Chemical Communications, 2015, vol. 51, # 81, p. 14996 - 14999]

19
[ 14316-14-4 ]
[ 123-38-6 ]
[ 1190398-17-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;

Reference： [1]Location in patent: experimental part Bates, Roderick W.; Lu, Yongna; Cai, Melody Peiling [Tetrahedron, 2009, vol. 65, # 37, p. 7852 - 7858]

20
[ 14316-14-4 ]
[ 870-63-3 ]
[ 1119121-89-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In acetone for 12h;
90%	With potassium carbonate In acetone for 12h;
81%	With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere;

62%	With potassium carbonate; potassium iodide In acetone for 16h; Reflux;
55%	With potassium carbonate; potassium iodide In acetone at 60℃; Schlenk technique; Inert atmosphere;

Reference： [1]Location in patent: scheme or table Jayagobi, Mathesan; Raghunathan, Raghavachary [Tetrahedron Letters, 2009, vol. 50, # 49, p. 6886 - 6890]
[2]Location in patent: scheme or table Jayagobi, Mathesan; Poornachandran, Mahalingam; Raghunathan, Raghavachary [Tetrahedron Letters, 2009, vol. 50, # 6, p. 648 - 650]
[3]Deka, Manash J.; Indukuri, Kiran; Sultana, Sabera; Borah, Madhurjya; Saikia, Anil K. [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4349 - 4359]
[4]Venning, Alexander R. O.; Kwiatkowski, Megan R.; Roque Peña, Joan E.; Lainhart, Brendan C.; Guruparan, Akil A.; Alexanian, Erik J. [Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11595 - 11600]
[5]Koy, Maximilian; Bellotti, Peter; Katzenburg, Felix; Daniliuc, Constantin G.; Glorius, Frank [Angewandte Chemie - International Edition, 2020, vol. 59, # 6, p. 2375 - 2379][Angew. Chem., 2020, vol. 132, p. 2395 - 2399,5]

21
[ 14316-14-4 ]
[ 4392-24-9 ]
N-cinnamyl-N-(2-hydroxyethyl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In acetone for 12h;
224 g	With potassium carbonate In acetone at 20℃; for 16h;
	With potassium carbonate In acetone Reflux;

	With potassium carbonate In acetone for 12h; Reflux; Inert atmosphere;
	With potassium carbonate In acetone Inert atmosphere;

Reference： [1]Location in patent: scheme or table Jayagobi, Mathesan; Raghunathan, Raghavachary [Tetrahedron Letters, 2009, vol. 50, # 49, p. 6886 - 6890]
[2]Bezanson, Michelle; Pottel, Joshua; Bilbeisi, Rana; Toumieux, Sylvestre; Cueto, Mickaël; Moitessier, Nicolas [Journal of Organic Chemistry, 2013, vol. 78, # 3, p. 872 - 885]
[3]Ghosh, Priya; Deka, Manash J.; Saikia, Anil K. [Tetrahedron, 2016, vol. 72, # 5, p. 690 - 698]
[4]Hwang, Joon Young; Baek, Jong Hwa; Shin, Tae Il; Shin, Jung Ha; Oh, Jae Won; Kim, Kwang Pyo; You, Youngmin; Kang, Eun Joo [Organic Letters, 2016, vol. 18, # 19, p. 4900 - 4903]
[5]Kuo, Jonathan L.; Lorenc, Chris; Abuyuan, Janine M.; Norton, Jack R. [Journal of the American Chemical Society, 2018, vol. 140, # 13, p. 4512 - 4516]

22
[ 142-26-7 ]
[ 98-59-9 ]
[ 16180-96-4 ]
[ 14316-14-4 ]
1-O-acetyl-2-(tosylamido)ethanol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 3515 - 3517

23
[ 141-43-5 ]
[ 2232-08-8 ]
[ 14316-14-4 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4232 - 4235

24
[ 5117-12-4 ]
[ 14316-14-4 ]
[ 1265900-15-9 ]