[ CAS No. 80-39-7 ] {[proInfo.proName]}

Name: 80-39-7|N-Ethyl-4-methylbenzenesulfonamide|98%
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SKU: A690478
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3d Animation Molecule Structure of 80-39-7

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Quality Control of [ 80-39-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 80-39-7 ]

Product Details of [ 80-39-7 ]

CAS No. :	80-39-7	MDL No. :	MFCD00048511
Formula :	C₉H₁₃NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OHPZPBNDOVQJMH-UHFFFAOYSA-N
M.W :	199.27	Pubchem ID :	6637
Synonyms :

Calculated chemistry of [ 80-39-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.11
TPSA :	54.55 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.34 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	1.65
Log Po/w (WLOGP) :	2.37
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	1.1 mg/ml ; 0.00551 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.777 mg/ml ; 0.0039 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.56
Solubility :	0.0551 mg/ml ; 0.000277 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 80-39-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 80-39-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 80-39-7 ]

[ 80-39-7 ] Synthesis Path-Downstream 1~88

1
[ 778-28-9 ]
[ 80-39-7 ]
[ 10285-92-4 ]

Reference： [1]Monatshefte fur Chemie,1952,vol. 83,p. 870,872,876

2
[ 75-04-7 ]
[ 98-59-9 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	In ethyl acetate at 0 - 20℃; for 1h;
90%	With triethylamine In dichloromethane
	With alkali

	With indole-3-carboxaldehyde-polystyrene resin; sodium cyanoborohydride; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride Yield given. Multistep reaction;
	In dichloromethane
	With triethylamine In dichloromethane at 0 - 10℃;
	With sodium carbonate In water at 20℃;

Reference： [1]Meyer, Andreas Uwe; Berger, Anna Lucia; König, Burkhard [Chemical Communications, 2016, vol. 52, # 72, p. 10918 - 10921]
[2]Zeng, Xianzhu; Tu, Yongliang; Zhang, Zhenming; You, Changming; Wu, Jiao; Ye, Zhiying; Zhao, Junfeng [Journal of Organic Chemistry, 2019, vol. 84, # 7, p. 4458 - 4466]
[3]Marckwald; v.Droste-Huelshoff [Chemische Berichte, 1899, vol. 32, p. 562] Remsen; Palmer [American Chemical Journal, 1886, vol. 8, p. 242]
[4]Estep, Kimberly G.; Neipp, Christopher E.; Stephens Stramiello, Linda M.; Adam, Mavis D.; Allen, Martin P.; Robinson, Shaughnessy; Roskamp, Eric J. [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5300 - 5301]
[5]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]
[6]Saidykhan, Amie; Ebert, Jenessa; Martin, William H.C.; Gallagher, Richard T.; Bowen, Richard D. [European Journal of Mass Spectrometry, 2016, vol. 22, # 4, p. 165 - 173]
[7]Hosseini, Raziyeh; Mohammadiannejad, Kazem; Ranjbar-Karimi, Reza [Journal of Fluorine Chemistry, 2020, vol. 233]

3
[ 80-39-7 ]
[ 599-91-7 ]
N-ethyl-4-methyl-N-propylbenzenesulfonamide [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1952,vol. 83,p. 870,872,876

4
[ 67-56-1 ]
[ 80-39-7 ]
[ 58754-95-3 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium methylate; potassium bromide at 25℃; anodic oxidation;
59%	With potassium hydroxide; potassium bromide anodic oxidation;

Reference： [1]Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Takeuchi, Kei; Sasaki, Katsushi; Kamada, Tohru; Shimizu, Rie [Journal of the American Chemical Society, 1990, vol. 112, # 6, p. 2368 - 2372]
[2]Shono, Tatsuya; Matsumura, Yoshihiro; Katoh, Susumu; Inoue, Kenji; Matsumoto, Yonetatsu [Tetrahedron Letters, 1986, vol. 27, # 50, p. 6083 - 6086]

5
[ 80-39-7 ]
[ 87010-92-2 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium <i>tert</i>-butylate; hydroxylamine-O-sulfonic acid In methanol; isopropyl alcohol for 0.5h;

Reference： [1]Hofer, Edgar; Keuper, Regina [Synthesis, 1983, # 6, p. 466 - 467]

6
[ 80-39-7 ]
[ 142-28-9 ]
[ 113812-28-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In N,N-dimethyl-formamide at 57℃; for 16h;
	In N,N-dimethyl-formamide	2 EXAMPLE 2 EXAMPLE 2 N-Ethyl-N-(3-chloropropyl)-p-toluenesulfonamide. To N-ethyl-p-toluenesulfonamide (5.01 g, 0.0251 mol) in DMF (50 mL) in a dry flask is added sodium hydride (80% in oil, 0.93 g, 0.031 mol). After gas evolution subsides, 1,3-dichloropropane (22.48 g, 0.199 mol) is added. The mixture is heated at 53°C. for 10 h then cooled and poured into ice water (300 mL), which is extracted twice with ether. The combined extracts are washed with 1% sodium bisulfite, water (3*), and brine. Removal of solvent by rotary evaporation then Kugelrohr distillation gives crude product, which is chromatographed on silica gel (30% hexane/CHCl3) to furnish 2.91 g product (42%) NMR (CDCl3)δ1.15 (t, 3H), 1.9-2.2 (m, 2H), 2.44 (s, 3H), 3.11-3.35 (m, 4H), 3.6 (t, 2H), 7.3 (d, 2H), 7.74 (d, 2H).

Reference： [1]Bergeron, Raymond J.; Neims, Allen H.; McManis, James S.; Hawthorne, Thomas R.; Vinson, John R. T.; et al. [Journal of Medicinal Chemistry, 1988, vol. 31, # 6, p. 1183 - 1190]
[2]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - US5091576, 1992, A

7
[ 675-14-9 ]
[ 80-39-7 ]
2-(N-ethyl-4-methylbenzenesulfonamido)-4,6-difluoro-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 2,4,6-trimethyl-pyridine In acetone at 20℃; for 48h;

Reference： [1]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]

8
[ 108-77-0 ]
[ 80-39-7 ]
4,6-dichloro-2-(N-ethyl-4-methylbenzenesulfonamido)-1,3,5-triazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium In ethanol for 0.5h; Stage #2: 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at -10 - 20℃; for 1h;

Reference： [1]Brewer, Stuart A.; Burnell, Helen T.; Holden, Ian; Jones, Brian G.; Willis, Colin R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1231 - 1234]

9
[ 80-39-7 ]
N-fluoro-N-ethyl-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium hydride In dichloromethane; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane; mineral oil at 20℃; for 6h; Inert atmosphere;
34%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With potassium hydride In dichloromethane at 24℃; for 0.5h; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane at 24℃; for 6h;
	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium hydride In dichloromethane at 0℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: With N-fluorobis(benzenesulfon)imide In dichloromethane at 0 - 20℃; for 24h; Schlenk technique; Inert atmosphere;

Reference： [1]Wang, Dinghai; Wu, Lianqian; Wang, Fei; Wan, Xiaolong; Chen, Pinhong; Lin, Zhenyang; Liu, Guosheng [Journal of the American Chemical Society, 2017, vol. 139, # 20, p. 6811 - 6814]
[2]Taylor, Dawne M.; Meier, G. Patrick [Tetrahedron Letters, 2000, vol. 41, # 18, p. 3291 - 3294]
[3]Ji, Yun-Xing; Li, Jinxia; Li, Chun-Min; Qu, Shuanglin; Zhang, Bo [Organic Letters, 2021, vol. 23, # 1, p. 207 - 212]

10
[ 80-39-7 ]
(S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane [ No CAS ]
[ 259656-68-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With 15-crown-5; sodium hydride; sodium iodide In N,N-dimethyl-formamide at 0 - 80℃; Stage #2: (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane In N,N-dimethyl-formamide at 80℃; for 70h; Further stages.;

Reference： [1]Bergeron, Raymond J.; Müller, Ralf; Bussenius, Jörg; McManis, James S.; Merriman, Ronald L.; Smith, Richard E.; Yao, Hua; Weimar, William R. [Journal of Medicinal Chemistry, 2000, vol. 43, # 2, p. 224 - 235]

11
[ 80-39-7 ]
[ 62871-09-4 ]
[ 309974-76-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With magnesium bromide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: 10-bromodec-1-ene In tetrahydrofuran at -78 - 20℃;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

12
[ 80-39-7 ]
[ 70-55-3 ]

Yield	Reaction Conditions	Operation in experiment
50%	With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 6h; Irradiation;
50%	With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 6h; ultrasonic irradiation;

Reference： [1]Katohgi, Masashi; Yokoyama, Masataka; Togo, Hideo [Synlett, 2000, # 7, p. 1055 - 1057]
[2]Katohgi, Masashi; Togo, Hideo [Tetrahedron, 2001, vol. 57, # 35, p. 7481 - 7486]

13
[ 80-39-7 ]
[ 224619-59-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With iodine In tetrahydrofuran at -78℃; for 0.5h;
78%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: With iodine In tetrahydrofuran; hexane at -78℃; Further stages.;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]
[2]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

14
[ 80-39-7 ]
[ 309974-83-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 0.5h; Stage #3: With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 16h;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

15
[ 80-39-7 ]
[ 106-95-6 ]
[ 309974-75-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: With magnesium bromide In tetrahydrofuran at -78℃; for 0.5h; Stage #3: allyl bromide In tetrahydrofuran at -78 - 20℃;

Reference： [1]Lane; Snieckus [Synlett, 2000, # 9, p. 1294 - 1296]

16
[ 75-77-4 ]
[ 80-39-7 ]
N-ethyl-4-trimethylsilylmethylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 20℃; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 1h; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

17
[ 75-77-4 ]
[ 80-39-7 ]
N-ethyl-4-methyl-2-trimethylsilylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 0℃; for 1h; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

18
[ 80-39-7 ]
2-deutero-N-ethyl-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: With d⁽⁴⁾-methanol In tetrahydrofuran; hexane at 0℃; for 1h; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

19
[ 80-39-7 ]
N-ethyl-4-deuteriomethylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: With d⁽⁴⁾-methanol In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction;
	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 20℃; Stage #2: With d⁽⁴⁾-methanol In tetrahydrofuran at 20℃; Further stages.;

Reference： [1]Fleming, Patricia; Oshea, Donal F. [Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1698 - 1701]
[2]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

20
[ 80-39-7 ]
[ 100-52-7 ]
N-ethyl-4-(2-hydroxy-2-phenylethyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran at -78 - 20℃; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 1h; Stage #3: With sodium tetrahydroborate In methanol at 0 - 20℃; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

21
[ 80-39-7 ]
[ 100-52-7 ]
N-ethyl-2-(hydroxyphenylmethyl)-4-methylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at 0℃; for 1h; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

22
[ 80-39-7 ]
[ 74-88-4 ]
[ 257953-14-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 1h; Further stages.;

Reference： [1]MacNeil; Familoni; Snieckus [Journal of Organic Chemistry, 2001, vol. 66, # 11, p. 3662 - 3670]

23
[ 80-39-7 ]
[ 100-44-7 ]
[ 25566-56-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 3h;

Reference： [1]Hu, Yi; Chen, Zhen-Chu; Le, Zhang-Gao; Zheng, Qin-Guo [Organic Preparations and Procedures International, 2004, vol. 36, # 4, p. 347 - 351]

24
[ 80-39-7 ]
[ 74-88-4 ]
[ 57186-68-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 3h;

Reference： [1]Hu, Yi; Chen, Zhen-Chu; Le, Zhang-Gao; Zheng, Qin-Guo [Organic Preparations and Procedures International, 2004, vol. 36, # 4, p. 347 - 351]

25
[ 16911-89-0 ]
[ 80-39-7 ]
C₁₆H₁₇NO₂S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: N-ethyl-4-methyl-benzenesulfonamide With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: phenyl chlorodithioformate In tetrahydrofuran at 20℃; for 24h;

Reference： [1]Norberto, Fatima; Araujo, M. Eduarda M.; Santos, Lidia; Jaime, Marta S. P.; Mateus, Pedro M. V.; Herves, Pablo [European Journal of Organic Chemistry, 2005, # 21, p. 4710 - 4714]

26
[ 5162-44-7 ]
[ 80-39-7 ]
[ 10285-79-7 ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium carbonate In acetonitrile for 12h; Heating;
972 mg	With potassium carbonate In acetonitrile for 2h; Reflux;

Reference： [1]Schmidt, Axel M.; Eilbracht, Peter [Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2333 - 2343]
[2]Dong, Xiang; Sang, Rui; Wang, Qiang; Tang, Xiang-Ying; Shi, Min [Chemistry - A European Journal, 2013, vol. 19, # 50, p. 16910 - 16915]

27
[ 80-39-7 ]
[ 106-95-6 ]
[ 863418-78-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium hydride In tetrahydrofuran for 1h; Heating;
1.254 g	With potassium carbonate In acetonitrile for 2h; Reflux;

28
[ 80-39-7 ]
[ 110-83-8 ]
[ 51210-13-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	In 1,2-dichloro-ethane at 140℃; for 1h; microwave irradiation;

Reference： [1]Liu, Xin-Yuan; Li, Cheng-Hui; Che, Chi-Ming [Organic Letters, 2006, vol. 8, # 13, p. 2707 - 2710]

29
sulfamic acid 2-[ethyl-(toluene-4-sulfonyl)-amino]-ethyl ester [ No CAS ]
sulfamic acid 2-(toluene-4-sulfonylamino)ethyl ester [ No CAS ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 59% 2: 25%	With [bis(acetoxy)iodo]benzene; magnesium oxide In dichloromethane at 40℃; for 6h;

Reference： [1]Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed [Organic Letters, 2006, vol. 8, # 20, p. 4493 - 4496]

30
[ 80-39-7 ]
[ 598-21-0 ]
[ 254986-03-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With zinc(II) chloride In toluene for 4h; Heating;

Reference： [1]Pospíšil, Jiří; Potáček, Milan [Tetrahedron, 2007, vol. 63, # 2, p. 337 - 346]

31
[ 21567-23-7 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ClSO₂NH₂; pyridine / CH₂Cl₂ / 0 - 20 °C 2: 25 percent / PhI(OAc)2; MgO / Rh₂(OAc)4 / CH₂Cl₂ / 6 h / 40 °C

Reference： [1]Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed [Organic Letters, 2006, vol. 8, # 20, p. 4493 - 4496]

32
[ 98-59-9 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetone; H₂O / 20 °C 2: ClSO₂NH₂; pyridine / CH₂Cl₂ / 0 - 20 °C 3: 25 percent / PhI(OAc)2; MgO / Rh₂(OAc)4 / CH₂Cl₂ / 6 h / 40 °C

Reference： [1]Toumieux, Sylvestre; Compain, Philippe; Martin, Olivier R.; Selkti, Mohamed [Organic Letters, 2006, vol. 8, # 20, p. 4493 - 4496]

33
[ 80-39-7 ]
<i>N</i>-ethyl-4-methyl-<i>N</i>-(2-methyl-3-oxo-propyl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 72 percent / NaH / tetrahydrofuran / 1 h / Heating 2: Xantphos; H₂ / Rh(acac)(CO)2 / tetrahydrofuran / 20 h / 70 °C / 15001.2 Torr

Reference： [1]Schmidt, Axel M.; Eilbracht, Peter [Organic and Biomolecular Chemistry, 2005, vol. 3, # 12, p. 2333 - 2343]

34
[ 349098-36-8 ]
[ 75-04-7 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorosulfonic acid; sodium hydroxide In water; toluene	4 Preparation of N-ethyl Toluenesulfonamide EXAMPLE 4 Preparation of N-ethyl Toluenesulfonamide A 1 liter flask equipped as for Example 3 was charged with 3.5 moles (407.8 gms) of chlorosulfonic acid, and 1.0 mole (92.1 gms) of toluene was added over a 1/2 hour period under N2 at 25° C. to 30° C. Stirring and cooling with an external cold water bath was required. The reaction mixture was then stirred at 25° C. under N2 for 4 hours. The resulting crude sulfonyl chloride mixture was added to a solution of 1.0 mole of ethylamine and 294 gms of NaOH in 900 ml of deionized water at 45° C. to 55° C. over a 2 hour period. The mixture was stirred at 55° C. and at a pH above 10 for 1 hour after the addition was completed. After standing overnight, the organic phase was separated, washed with water, decolorized with potassium permanganate and sodium meta bisulfite, washed with sodium carbonate solution and water, and dehydrated at 125° C. and 0.2 mm Hg (26.66 Pa), giving 123g (61.7% yield) of light yellow liquid. Proton NMR in CDCl3 was consistent with the N-ethyl toluene sulfonamide structure. GC analysis showed 43.5 percent ortho and 53.3 percent para-N-ethyl toluene sulfonamide plus 2.4 percent tolyl sulfones.

Reference： [1]Current Patent Assignee: AKZO NOBEL NV - US4713489, 1987, A

35
[ 80-39-7 ]
[ 100-46-9 ]
[ 112193-79-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate	1.3.13.20 1,7-Bis(p-toluenesulfonyl)-4-benzyl-1,4,7-triazaheptane. 1.3.13.20 1,7-Bis(p-toluenesulfonyl)-4-benzyl-1,4,7-triazaheptane. From benzylamine, (2-p-toluenesulfonyoxyl)-N-(p-toluenesulfonyl)-ethylamine (1.3.13.21) and potassium carbonate.
	With potassium carbonate	11.3.13.20 1,7-Bis(p-toluenesulfonyl)-4-benzyl-1,4,7-triazaheptane. 11.3.13.20 1,7-Bis(p-toluenesulfonyl)-4-benzyl-1,4,7-triazaheptane. From benzylamine, (2-p-toluenesulfonyoxyl)-N-(p-toluenesulfonyl)-ethylamine (1.3.13.21) and potassium carbonate.

Reference： [1]Current Patent Assignee: CHELATOR - US6264966, 2001, B1
[2]Current Patent Assignee: CONCAT; CHELATOR - US2004/6055, 2004, A1

36
[ 64-17-5 ]
[ 70-55-3 ]
[ 80-39-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With perchloric acid adsorbed on silica gel In 1,4-dioxane at 80℃; for 3h;	General experimental procedure for N-alkylation of amides General procedure: To a mixture of an alcohol (1.0 mmol) and an amide (1.2 mmol) in 1,4-dioxane (2 ml) HClO4·SiO2 (50 mg) was added. The mixture was stirred at 80 °C and the reaction was monitored by TLC. After completion the mixture was filtered to recover the catalyst and the residue was washed with EtOAc (3 × 5 ml). The combined organic portion was subjected to column chromatography (silica gel, hexane-EtOAc) to obtain a pure N-alkylated amide.
66%	With phosphotungstic acid 44-hydrate at 140℃; for 4h;
34%	With [Mn(HN(C₂H₄PⁱPr₂)₂)(CO)₂Br]; potassium carbonate at 150℃; for 24h; Sealed tube;

Reference： [1]Location in patent: experimental part Das, Biswanath; Reddy, Parigi Raghavendar; Sudhakar, Chithaluri; Lingaiah, Maram [Tetrahedron Letters, 2011, vol. 52, # 27, p. 3521 - 3522]
[2]Location in patent: experimental part Wang, Guan-Wu; Shen, Ye-Bing; Wu, Xue-Liang [European Journal of Organic Chemistry, 2008, # 25, p. 4367 - 4371]
[3]Reed-Berendt, Benjamin G.; Morrill, Louis C. [Journal of Organic Chemistry, 2019, vol. 84, # 6, p. 3715 - 3724]

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[ 4224-87-7 ]
[ 80-39-7 ]
3-bromo-3-(4-methylphenyl)-1-phenyl-2-(N-ethyltosylamino)propan-1-one [ No CAS ]