Name: 57683-71-3|Methyl 2-(Aminosulfonyl)benzoate|98%
Brand: Ambeed
SKU: A349785
Rating: 91 (32 reviews)

1
[ 67-56-1 ]
[ 632-24-6 ]
[ 57683-71-3 ]

Reference： [1]Patent: DE101483,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 5,p. 877
[2]American Chemical Journal,1889,vol. 11,p. 334

2
[ 67-56-1 ]
[ 81-07-2 ]
[ 57683-71-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sulfuric acid at 10 - 70℃; for 12h;	2.a; 4.a Example 2 (a) In a 250 mL three-necked flask, add 25 g of I at room temperature,100mL of methanol, start stirring, and control the temperature between 10 -25 ,Slowly add 8.03g of concentrated sulfuric acid.The reaction system started to warm to 70 ° C and reacted for 12 hours;After the reaction is completed, the temperature is lowered to room temperature.Recrystallization gave 26.14 g of white solid IV,Yield 89%,
65%	With sulfuric acid In methanol for 12h; Reflux;
	at 170℃;

	With hydrogenchloride for 8h;
	With hydrogenchloride for 8h; Heating;
	With sulfuric acid

Reference： [1]Current Patent Assignee: HEBEI XINGBAI AGRICULTURAL TECH - CN110437112, 2019, A Location in patent: Paragraph 0085-0090; 0105-0108
[2]Lee, Yu-Ting; Cui, Chang-Jun; Chow, Eve W. L.; Pue, Nason; Lonhienne, Thierry; Wang, Jian-Guo; Fraser, James A.; Guddat, Luke W. [Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 210 - 219]
[3]Hoogewerff; van Dorp [Recueil des Travaux Chimiques des Pays-Bas, 1899, vol. 18, p. 360][Chemisches Zentralblatt, 1899, vol. 70, # I, p. 251]
[4]Bhattacharjee; Dureja [Chemosphere, 1999, vol. 38, # 4, p. 741 - 749]
[5]Bhattacherjee; Dureja [Pesticide Science, 1999, vol. 55, # 2, p. 183 - 188]
[6]Wang, Bao-Lei; Shi, Yan-Xia; Zhang, Shu-Jun; Ma, Yi; Wang, Hong-Xue; Zhang, Li-Yuan; Wei, Wei; Liu, Xing-Hai; Li, Yong-Hong; Li, Zheng-Ming; Li, Bao-Ju [European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178]

3
[ 74223-64-6 ]
[ 93-58-3 ]
[ 57683-71-3 ]
[ 74222-95-0 ]
[ 1668-54-8 ]
2-Isocyanato-4-methoxy-6-methyl-[1,3,5]triazine [ No CAS ]
[ 18712-14-6 ]

Reference： [1]Journal of Mass Spectrometry,1995,vol. 30,p. 333 - 338

4
[ 26638-43-7 ]
[ 57683-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In acetonitrile; at 0 - 20℃; for 1h;Inert atmosphere;	General procedure: In a 50 ml RB flask, sulfonyl chloride (500 mg) was taken in acetonitrile (5 ml) and the solution was cooled to 0 deg. Cel. To this aqueous ammonia solution (1.5 ml) was added dropwise. RM was then stirred at RT for 1 hr. RM was evaporated to dryness and the residue was then trichirated with minimum water and suspension was filtered and solid was dried to get the sulfonamide as solid.

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1145 - 1148
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2222 - 2225

5
[ 57683-71-3 ]
[ 100-52-7 ]
2-[1-Phenyl-meth-(E)-ylidene]-sulfamoyl}-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With K 10 clay; calcium carbonate; trimethyl orthoformate at 180 - 183℃; for 0.133333h; Irradiation;

Reference： [1]Vass, Andras; Dudas, Jozsef; Varma, Rajender S. [Tetrahedron Letters, 1999, vol. 40, # 27, p. 4951 - 4954]

6
[ 74223-64-6 ]
[ 57683-71-3 ]
[ 1668-54-8 ]
methyl 2-[[[[(4-hydroxy-6-methyl-1,3,5-triazine-2-yl)amino]carbonyl]amino]sulfonyl]benzoate [ No CAS ]
methyl 2-[[[[[[[(acetylamino)carbonyl]amino]carbonyl]amino]carbonyl]amino]sulfonyl]benzoate [ No CAS ]

Reference： [1]Analytical Chemistry,2001,vol. 73,p. 4403 - 4409

7
[ 57683-71-3 ]
[ 10191-60-3 ]
methyl 2-([(cyanoimino)(methylsulfanyl)methyl]amino}sulfonyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: methyl 2-(aminosulfonyl)benzoate; dimethyl N-cyanodithioiminocarbonate With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 8h;

Reference： [1]Chibale, Kelly; Dauvergne, Jérôme; Wyatt, Paul G. [Synthesis, 2002, # 2, p. 185 - 190]

8
[ 542-08-5 ]
[ 57683-71-3 ]
(1-methylethyl)-4-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: isopropyl acetoacetate With lithium diisopropyl amide In tetrahydrofuran for 1h; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 0℃; for 3h;
78%	Stage #1: isopropyl acetoacetate; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Meierhoefer, Michelle A.; Walters, Matthew J.; Beam, Charles F. [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 295 - 298]
[2]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

9
[ 57683-71-3 ]
[ 917-54-4 ]
[ 34989-82-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	In tetrahydrofuran at 0 - 20℃;

Reference： [1]Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Meierhoefer, Michelle A.; Walters, Matthew J.; Beam, Charles F. [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 295 - 298]

10
[ 57683-71-3 ]
[ 102-01-2 ]
N-phenyl 4-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: N-phenylacetoacetamide With lithium diisopropyl amide In tetrahydrofuran for 3h; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 20℃; for 3h;

Reference： [1]Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Meierhoefer, Michelle A.; Walters, Matthew J.; Beam, Charles F. [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 295 - 298]

11
[ 57683-71-3 ]
[ 591-51-5 ]
[ 53440-57-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	In tetrahydrofuran at 0 - 20℃;

Reference： [1]Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Meierhoefer, Michelle A.; Walters, Matthew J.; Beam, Charles F. [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 295 - 298]

12
[ 57683-71-3 ]
[ 93-91-4 ]
4-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-1-phenylbutan-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 1-phenylbutan-1,3-dione With lithium diisopropyl amide In tetrahydrofuran for 1h; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 0℃; for 3h;

Reference： [1]Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Meierhoefer, Michelle A.; Walters, Matthew J.; Beam, Charles F. [Journal of Heterocyclic Chemistry, 2004, vol. 41, # 2, p. 295 - 298]

13
[ 57683-71-3 ]
[ 102169-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In methanol at 20℃;

Reference： [1]Winum, Jean-Yves; Dogné, Jean-Michel; Casini, Angela; De Leval, Xavier; Montero, Jean-Louis; Scozzafava, Andrea; Vullo, Daniela; Innocenti, Alessio; Supuran, Claudiu T. [Journal of Medicinal Chemistry, 2005, vol. 48, # 6, p. 2121 - 2125]

14
[ 57683-71-3 ]
[ 1788-30-3 ]
2-(1,4-diphenyl-3-phenylmethyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: phenylhydrazone of dibenzyl ketone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

15
[ 57683-71-3 ]
[ 59130-82-4 ]
2-(1,3-diphenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: acetophenone phenylhydrazone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

16
[ 57683-71-3 ]
[ 58697-62-4 ]
2-(3-(3,4-dimethoxyphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 1-(3,4-dimethoxy-phenyl)-ethanone-phenylhydrazone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

17
[ 57683-71-3 ]
1-(3,4,5-trimethoxy-phenyl)-ethanone-phenylhydrazone [ No CAS ]
2-(3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 1-(3,4,5-trimethoxy-phenyl)-ethanone-phenylhydrazone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

18
[ 57683-71-3 ]
(E)-1-phenyl-2-(1-(p-tolyl)ethylidene)hydrazine [ No CAS ]
2-(3-(4-methylphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: (E)-1-phenyl-2-(1-(p-tolyl)ethylidene)hydrazine With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

19
[ 57683-71-3 ]
2-acetonaphthonephenylhydrazone [ No CAS ]
2-(3-(2-naphthyl)-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-acetonaphthonephenylhydrazone With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

20
[ 57683-71-3 ]
[ 117788-17-7 ]
2-(3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (E)-1-(1-(4-methoxyphenyl)ethylidene)-2-phenylhydrazine With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 0℃;

Reference： [1]Meierhoefer, Michelle A.; Dunn, S. Patrick; Hajiaghamohseni, Laela M.; Walters, Matthew J.; Embree, Mildred C.; Grant, Sally P.; Downs, Jennifer R.; Townsend, Jessica D.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2005, vol. 42, # 6, p. 1095 - 1099]

21
[ 609-14-3 ]
[ 57683-71-3 ]
ethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-2-methyl-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-acetylpropanoic acid ethyl ester; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

22
[ 517-23-7 ]
[ 57683-71-3 ]
2-(1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidene)-1-(dihydro-2-oxo-2(3H)-furan-3-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	Stage #1: 3-acetyl-2-oxo-4,5-dihydrofuran; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

23
[ 1694-31-1 ]
[ 57683-71-3 ]
1,1-dimethylethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: tert-butyl acetoacetate; methyl 2-(aminosulfonyl)benzoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

24
[ 57683-71-3 ]
[ 141-97-9 ]
ethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: methyl 2-(aminosulfonyl)benzoate; ethyl acetoacetate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

25
[ 57683-71-3 ]
[ 105-45-3 ]
methyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: methyl 2-(aminosulfonyl)benzoate; acetoacetic acid methyl ester With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

26
[ 57683-71-3 ]
[ 620-79-1 ]
ethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-2-phenyl-methyl-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: methyl 2-(aminosulfonyl)benzoate; Ethyl 2-benzylacetoacetate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

27
[ 57683-71-3 ]
[ 607-97-6 ]
ethyl (1,1-dioxido-1,2-benzisothiazol-3(2H)-ylidine)-2-ethyl-3-oxo-butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: methyl 2-(aminosulfonyl)benzoate; ethyl 2-ethyl-3-oxobutanoate With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With hydrogenchloride In tetrahydrofuran

Reference： [1]Meierhoefer, Michelle A.; Walters, Matthew J.; Dunn, S. Patrick; Vella, Jarrett H.; Grant, Bonnie J.; Sober, Carolyn L.; Patel, Nidhi S.; Hajiaghamohseni, Laela M.; Lioi, Sara B.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 2, p. 307 - 313]

28
[ 496-11-7 ]
[ 57683-71-3 ]
2-(indan-1-ylsulfamoyl)-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tert.butyl-peroxyacetate; 4 A molecular sieve; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 60℃; for 6h;

Reference： [1]Pelletier, Guillaume; Powell, David A. [Organic Letters, 2006, vol. 8, # 26, p. 6031 - 6034]

29
[ 57683-71-3 ]
[ 104-87-0 ]
[ 951762-80-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	Heating;

Reference： [1]Castellano, Sabrina; Fiji, Hannah D. G.; Kinderman, Sape S.; Watanabe, Masaru; De Leon, Pablo; Tamanoi, Fuyuhiko; Kwon, Ohyun [Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5843 - 5845]

30
[ 57683-71-3 ]
[ 123-11-5 ]
[ 951762-75-7 ]

Yield	Reaction Conditions	Operation in experiment
36%	Heating;

Reference： [1]Castellano, Sabrina; Fiji, Hannah D. G.; Kinderman, Sape S.; Watanabe, Masaru; De Leon, Pablo; Tamanoi, Fuyuhiko; Kwon, Ohyun [Journal of the American Chemical Society, 2007, vol. 129, # 18, p. 5843 - 5845]

31
[ 98320-74-2 ]
[ 57683-71-3 ]
[ 139-02-6 ]
[ 74223-63-5 ]

Yield	Reaction Conditions	Operation in experiment
82.2%	Stage #1: 4,6-dimethoxy-1,3,5-triazin-2-yl-carbamic acid,phenyl ester; methyl 2-(aminosulfonyl)benzoate; sodium phenoxide In N,N-dimethyl acetamide for 1.58333h; Stage #2: With hydrogenchloride In N,N-dimethyl acetamide; water at 0℃;

Reference： [1]Current Patent Assignee: KUREHA CORP. - EP1209153, 2002, A2 Location in patent: Example 2

32
[ 34619-03-9 ]
[ 57683-71-3 ]
[ 140617-83-0 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dmap; triethylamine In dichloromethane at 20℃; for 2h;

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2004/54974, 2004, A2 Location in patent: Page 433

33
6-bromo-5-methoxy-2-pyridinecarboxlic acid [ No CAS ]
[ 57683-71-3 ]
2-[[[(6-Bromo-5-methoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%		S.40 Synthesis of 2-[[[(6-Bromo-5-methoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic acid methyl ester [Compound (1-265)] Synthesis Example 40 Synthesis of 2-[[[(6-Bromo-5-methoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic acid methyl ester [Compound (1-265)] Using 2-(aminosulfonyl)benzoic acid methyl ester [Compound (III-3)] (0.278 g, 1.29 mmol) and 6-bromo-5-methoxy-2-pyridine-carboxlic acid [Compound (II-85)], the Compound (I-265) was synthesised according to the process of Synthesis Example 3. White solid, m.p.: 178-179° C., yield: 0.36 g, percent yield: 66.0%. IR KBr cm-1: 3358, 1725, 1569, 1404, 1359, 1275, 1185, 1074, 594. 1H-NMR (60 MHz, CDCl3, δ): 3.9 (3H, s, COOCH3 or OCH3), 4.0 (3H, s, COOCH3 or OCH3), 7.15 (1H, d, J=8 Hz, pyridine ring H), 7.38-7.75 (3H, m, aromatic ring H), 8.0 (1H, d, J=8 Hz, pyridine ring H), 8.06-8.46 (1H, m, aromatic ring H) NH indistinctness.

Reference： [1]Current Patent Assignee: KUREHA CORP. - US6610853, 2003, B1

34
6-chloro-2-pyridinecarboxyolic acid phenyl ester [ No CAS ]
[ 57683-71-3 ]
2-[[[(6-Chloropyridin-2-yl)carbonyl]amino]-sulfonyl]benzoic Acid Methyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.7%		S.51 Synthesis of 2-[[[(6-Chloropyridin-2-yl)carbonyl]amino]-sulfonyl]benzoic Acid Methyl Ester [Compound (I-231)] Synthesis Example 51 Synthesis of 2-[[[(6-Chloropyridin-2-yl)carbonyl]amino]-sulfonyl]benzoic Acid Methyl Ester [Compound (I-231)] Using 2-methoxycarbonylphenylsulfonamide [Compound (III-3)] (0.319 g, 1.48 mmol) and 6-chloro-2-pyridinecarboxyolic acid phenyl ester [Compound (IV-51)] (0.346 g, 1.48 mmol), the Compound (I-231) was synthesised according to the process of Synthesis Example 1. White solid, m.p.: 122-124° C., yield: 0.29 g, percent yield: 55.7%. IR KBr cm-1: 3328, 1746, 1725, 1452, 1185, 1062, 756. 1H-NMR (60 MHz, CDCl3, δ): 4.0 (3H, s, OCH3), 7.30-8.06 (6H, m, aromatic ring 3H, pyridine ring 3H), 8.06-8.46 (1H, m, aromatic ring H), 10.1-10.7 (1H, br, NH).

Reference： [1]Current Patent Assignee: KUREHA CORP. - US6610853, 2003, B1

35
[ 29082-92-6 ]
[ 57683-71-3 ]
[ 204378-16-5 ]

Yield	Reaction Conditions	Operation in experiment
16.5%		Synthesis Example 7 Synthesis of 2-[[[(5-Methoxypyridin-2-yl)carbonyl]amino]-sulfonyl]benzoic Acid Methyl Ester [Compound (I-234)] Using 2-methoxycarbonylbenzenesulfonamide [Compound (III-3)] (0.422 g, 1.96 mmol) and <strong>[29082-92-6]5-methoxypicolinic acid</strong> [Compound (II-54)] (0.3 g, 1.96 mmol), the Compound (I-234) was synthesised according to the process of Synthesis Example 3. White solid, yield: 0.113 g, percent yield: 16.5%, m.p.: 164-165 C. IR KBr cm-1: 3316, 1746, 1707, 1392, 1353, 1278, 1179. 1H-NMR (60 MHz, CDCl3, delta): 3.81 (3H, s, COOCH3 or OCH3), 3.9 (3H, s, COOCH3 or OCH3), 7.15 (1H, dd, J=3 Hz, 9 Hz, pyridine ring H), 7.35-7.65 (3H, m, aromatic ring H), 7.95 (1H, d, J=9 Hz, pyridine ring H), 8.15 (1H, d, J=3 Hz, pyridine ring H), 8.13-8.36 (1H, m, aromatic ring H), NH indistinctness.

Reference： [1]Patent: US6610853,2003,B1

36
[ 57683-71-3 ]
[ 90764-84-4 ]
[ 204378-19-8 ]

Yield	Reaction Conditions	Operation in experiment
75.6%		Synthesis Example 8 Synthesis of 2-[[[(4,6-Dimethoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-257)] Using 2-methoxycarbonylbenzenesulfonamide [Compound (III-3)] (0.106 g, 0.49 mmol) and <strong>[90764-84-4]4,6-dimethoxypicolinic acid</strong> [Compound (II-77)] (0.09 g, 0.49 mmol), the Compound (I-257) was synthesised according to the process of Synthesis Example 3. White solid, yield: 0.14 g, percent yield: 75.6%, m.p.: 156-158 C. IR KBr cm-1: 1728, 1617, 1473, 1392, 1347, 1293, 1182. 1H-NMR (60 MHz, CDCl3, delta): 3.73 (3H, s, OCH3 or COOCH3), 3.9 (3H, s, OCH3 or COOCH3), 4.0 (3H, s, OCH3), 6.3 (1H, d, J=2 Hz, pyridine ring H), 7.2 (1H, d, J=2 Hz, pyridine ring H), 7.5-7.8 (3H, m, aromatic ring H), 8.1-8.5 (1H, m, aromatic ring H), NH indistinctness.

Reference： [1]Patent: US6610853,2003,B1

37
[ 112750-30-8 ]
[ 57683-71-3 ]
[ 204378-20-1 ]

Yield	Reaction Conditions	Operation in experiment
43.1%		S.9 Synthesis of 2-[[[(6-Chloro-5-methoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-258)] Synthesis Example 9 Synthesis of 2-[[[(6-Chloro-5-methoxypyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-258)] Using 2-methoxycarbonylbenzenesulfonamide [Compound (III-3)] (0.344 g, 1.6 mmol) and 6-chloro-5-methoxypicolinic acid [Compound (II-78)] (0.3 g, 1.6 mmol), the Compound (I-258) was synthesised according to the process of Synthesis Example 3. White solid, yield: 0.26 g, percent yield: 43.1%, m.p.: 180-183° C. IR KBr cm-1: 3364, 1740, 1713, 1440, 1407, 1362, 1275, 1182, 1059, 855. 1H-NMR (60 MHz, CDCl3, δ): 3.9 (3H, s, COOCH3 or OCH3), 3.96 (3H, s, COOCH3 or OCH3), 7.16 (1H, d, J=8 Hz, pyridine ring H), 7.4-7.7 (3H, m, aromatic ring H), 7.9 (1H, d, J=8 Hz, pyridine ring H), 8.1-8.4 (1H, m, aromatic ring H), 10-10.5 (1H, bs, NH).

Reference： [1]Current Patent Assignee: KUREHA CORP. - US6610853, 2003, B1

38
[ 324028-93-5 ]
[ 57683-71-3 ]
2-[[[(3,6-Dichloropyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.2%	With potassium carbonate	S.68 Synthesis of 2-[[[(3,6-Dichloropyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-189)] Synthesis Example 68 Synthesis of 2-[[[(3,6-Dichloropyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-189)] Using 2-methoxycarbonylphenylsulfonamide [Compound (III-3)] (0.16 g, 0.745 mmol), 3,6-dichloro-2-pyridinecarboxylic acid phenyl ester [Compound (IV-9)] (0.2 g, 0.745 mmol) and potassium carbonate (0.126 g, 0.745 mmol), the Compound (I-189) was synthesised according to the process of Synthesis Example 1. White solid, m.p.: 154-155° C., yield: 0.32 g, percent yield: 77.2% IR KBr cm-1: 3328, 1755, 1734, 1446, 1350, 1296, 1179, 1032. 1H-NMR (60 MHz, d6-DMSO, δ): 3.9 (3H, s, COOCH3), 7.3 (1H, d, J=8 Hz, pyridine ring H), 7.3-7.7 (4H, m, aromatic ring H), 7.7 (1H, d, J=8 Hz, pyridine ring H), NH indistinctness.

Reference： [1]Current Patent Assignee: KUREHA CORP. - US6610853, 2003, B1

39
[ 324028-94-6 ]
[ 57683-71-3 ]
2-[[[(6-Chloro-4-methylpyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.2%	With potassium carbonate	S.74 Synthesis of 2-[[[(6-Chloro-4-methylpyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-188)] Synthesis Example 74 Synthesis of 2-[[[(6-Chloro-4-methylpyridin-2-yl)carbonyl]-amino]sulfonyl]benzoic Acid Methyl Ester [Compound (I-188)] Using 2-methoxycarbonylphenylsulfonamide [Compound (III-3)] (0.174 g, 0.808 mmol), 6-chloro-4-methylpicolinic acid phenyl ester [Compound (IV-8)] (0.2 g, 0.808 mmol) and potassium carbonate (0.11 g, 0.808 mmol), the Compound (I-188) was synthesised according to the process of Synthesis Example 1. White solid, m.p.: 160-163° C., yield: 0.17 g, percent yield: 57.2%. IR KBr cm-1: 3352, 1725, 1602, 1446, 1356, 1299, 1176, 1140, 1122, 888. 1H-NMR (60 MHz, CDCl3, δ): 2.4 (3H, s, CH3), 4.0 (3H, s, COOCH3), 7.1-7.8 (5H, m, aromatic ring H3, pyridine ring H2), 8.1-8.4 (1H, m, aromatic ring H), NH indistinctness.

Reference： [1]Current Patent Assignee: KUREHA CORP. - US6610853, 2003, B1

40
[ 49783-84-8 ]
[ 57683-71-3 ]
[ 745761-41-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In water; acetone	1 N-(2-Methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide EXAMPLE 1 N-(2-Methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide 10.8 g of 2-methoxycarbonylphenylsulfonamide, 8.6 g of 1,5-dimethylpyrazole-3-carbonyl chloride and 13.8 g of potassium carbonate in 200 ml of absolute acetone are refluxed for 8 h. The solvent is removed by distillation and then the residue is taken up in water and the pH is adjusted to 2. The precipitate is filtered off with suction and washed with H2 O until neutral. The residue is stirred with ether, filtered off with suction and dried under reduced pressure. 11.6 g of N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide with a melting point of 176°-177° C. are obtained (active ingredient Example No. 40).

Reference： [1]Current Patent Assignee: BASF SE - US5252540, 1993, A

41
[ 133185-43-0 ]
[ 57683-71-3 ]
N₁-(2,6-dichloro-7-methyl-8-purinyl)-2-carbomethoxybenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine	4 Synthesis of N1 -(2,6-dichloro-7-methyl-8-purinyl)-2-carbomethoxybenzenesulfonamide (process B) EXAMPLE 4 Synthesis of N1 -(2,6-dichloro-7-methyl-8-purinyl)-2-carbomethoxybenzenesulfonamide (process B) At 70° C., 6.60 g (28 mmol) of 2-carbomethoxybenzenesulfonamide was added to a suspension of 3.00 g (14.0 mmol) of 8-amino-2,6-dichloro-7-methylpurine in 150 ml of pyridine. After 3 hours at 70°-80° C., the reaction mixture was evaporated down in a rotary evaporator, and the residue was stirred into ice/H2 O and acidified with dilute HCl. The desired product was obtained in the form of a brown powder having the following physical data (active ingredient 1.020) 1 H-NMR (250 MHz, d6 -DMSO, δ in ppm): 3.60 (s, 3H, N-CH3); 3.80 (s, 3H, CO2 CH3); 7.60 (mc, 1H, aryl-H); 7.70 (mc, 2H, aryl-H); 8.10 (mc, 1H, aryl-H).

Reference： [1]Current Patent Assignee: BASF SE - US5171353, 1992, A

42
[ 280-57-9 ]
[ 57683-71-3 ]
[ 111-36-4 ]
[ 74222-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene	5 Methyl 2-(isocyanatosulfonyl)benzoate EXAMPLE 5 Methyl 2-(isocyanatosulfonyl)benzoate A stirred mixture containing 157 g of methyl 2-sulfamoylbenzoate, 73 g of butyl isocyanate 0.3 g of 1,4-diazabicyclo[2,2,2]octane and 1.0 l of xylene was heated to reflux for one half hour. Phosgene gas was then passed into the system under a dry ice reflux condenser allowing the reaction temperature to drop to 120°. This addition was continued until the reflux temperature remained at 120° without further phosgene addition. The temperature of the reaction mixture was then raised to 136° (by removal of the dry ice reflux condenser) after which it was cooled to room temperature and filtered. Evaporation of the filtrate yielded the desired crude sulfonyl isocyanate which could be purified by distillation at 132°-138° C. under 1.0 to 1.1 mm of mercury pressure.
	In 5,5-dimethyl-1,3-cyclohexadiene	1 Methyl 2-(isocyanatosulfonyl)benzoate EXAMPLE 1 Methyl 2-(isocyanatosulfonyl)benzoate A stirred mixture containing 157 g of methyl 2-sulfamoylbenzoate, 73 g of butyl isocyanate, 0.3 g of 1,4-diazabicyclo[2,2,2]octane and 1.0 l of xylene was heated to reflux for one half hour. Phosgene gas was then passed into the system under a dry ice reflux condenser allowing the reaction temperature to drop to 120°. This addition was continued until the reflux temperature remained at 120° without further phosgene addition. The temperature of the reaction mixture was then raised to 136° (by removal of the dry ice reflux condenser) after which it was cooled to room temperature and filtered. Evaporation of the filtrate yielded the desired crude sulfonyl isocyanate which could be purified by distillation at 132°-138° C. under 1.0 to 1.1 mm of mercury pressure.
	In 5,5-dimethyl-1,3-cyclohexadiene	5 Methyl 2-(isocyanatosulfonyl)benzoate EXAMPLE 5 Methyl 2-(isocyanatosulfonyl)benzoate A stirred mixture containing 157 g of methyl 2-sulfamoylbenzoate, 73 g of butyl isocyanate 0.3 g of 1,4-diazabicyclo[2,2,2,]octane and 1.0 l of xylene was heated to reflux for one half hour. Phosgene gas was then passed into the system under a dry ice reflux condenser allowing the reaction temperature to drop to 120°. This addition was continued until the reflux temperature remained at 120° without further phosgene addition. The temperature of the reaction mixture was then raised to 136° (by removal of the dry ice reflux condenser) after which it was cooled to room temperature and filtered. Evaporation of the filtrate yielded the desired crude sulfonyl isocyanate which could be purified by distillation at 132°-138° C. under 1.0 to 1.1 mm of mercury pressure.

In 5,5-dimethyl-1,3-cyclohexadiene

1 Methyl 2-(isocyanatosulfonyl)benzoate EXAMPLE 1 Methyl 2-(isocyanatosulfonyl)benzoate A stirred mixture containing 157 g of methyl 2-sulfamoylbenzoate, 73 g of butyl isocyanate 0.3 g of 1,4-diazabicyclo[2,2,2]octane and 1.0 l of xylene was heated to reflux for one half hour. Phosgene gas was then passed into the system under a dry ice reflux condenser allowing the reaction temperature to drop to 120°. This addition was continued until the reflux temperature remained at 120° without further phosgene addition. The temperature of the reaction mixture was then raised to 136° (by removal of the dry ice reflux condenser) after which it was cooled to room temperature and filtered. Evaporation of the filtrate yielded the desired crude sulfonyl isocyanate which could be purified by distillation at 132°-138° C. under 1.0 to 1.1 mm of mercury pressure.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US4293330, 1981, A
[2]Current Patent Assignee: DUPONT DE NEMOURS INC - US4370480, 1983, A Current Patent Assignee: DUPONT DE NEMOURS INC - US4342587, 1982, A
[3]Current Patent Assignee: DUPONT DE NEMOURS INC - US4372778, 1983, A
[4]Current Patent Assignee: DUPONT DE NEMOURS INC - US4238621, 1980, A Current Patent Assignee: DUPONT DE NEMOURS INC - US4394506, 1983, A Current Patent Assignee: DUPONT DE NEMOURS INC - US4818278, 1989, A

43
6,7-dihydro-2-isothiocyanato-4-methoxy-5H-cyclopentapyrimidine [ No CAS ]
[ 57683-71-3 ]
[ 76881-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate In water; acetone	10 Methyl 2-[[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminothioxomethyl]aminosulfonyl]benzoate EXAMPLE 10 Methyl 2-[[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminothioxomethyl]aminosulfonyl]benzoate A mixture of 4.3 g of methyl 2-(aminosulfonyl)-benzoate, 4.2 g of 6,7-dihydro-2-isothiocyanato-4-methoxy-5H-cyclopentapyrimidine and 2.2 g of anhydrous potassium carbonate in 70 ml of acetone was warmed to 40° with stirring. After 2 hours, a thick precipitate formed and stirring was continued for three more hours at ambient temperature. The precipitate was filtered, suspended in 150 ml of water, stirred and the pH adjusted to 2 by the addition of hydrochloric acid. The white solid was filtered, washed with cold water and dried to yield 4.2 g of product.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US4339267, 1982, A

44
3-bromo-6,8-dimethylimidazo[1,2-b]pyridazine [ No CAS ]
[ 79-37-8 ]
[ 57683-71-3 ]
methyl 2-((6,8-dimethylimidazo[1,2-b]pyridazin-3-ylcarbonyl)aminosulfonyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; carbon dioxide; triethylamine In tetrahydrofuran; dichloromethane; water	15 Methyl 2-((6,8-dimethylimidazo[1,2-b]pyridazin-3-ylcarbonyl)aminosulfonyl)benzoate EXAMPLE 15 Methyl 2-((6,8-dimethylimidazo[1,2-b]pyridazin-3-ylcarbonyl)aminosulfonyl)benzoate To a solution of 2.0 g (8.8 mmol) of 3-bromo-6,8-dimethylimidazo[1,2-b]pyridazine in 50 mL of tetrahydrofuran at -78° C. was added 6.1 mL (9.7 mmol) of a 1.6M solution of n-butyllithium in hexanes. After 15 min, carbon dioxide was bubbled through the solution for 10 min. After warming to room temperature, the solid material was isolated by filtration and washed with 1 mL of water. After drying overnight in a vacuum desiccator, 1.48 g of a solid was obtained. To a slurry of 0.5 g (2.5 mmol) of the solid obtained above in 8 mL of dichloromethane was added 1 mL oxalyl chloride. This mixture was heated to reflux for 2 h. After cooling, the volatiles were removed with a rotary evaporator and vacuum pump. The residue was dissolved in 6 mL of dichloromethane and was cooled in an ice bath. To this solution was added 0.55 g (2.5 mmol) of methyl 2-(aminosulfonyl)-benzoate and 0.36 mL (2.6 mmol) of triethylamine. The reaction was stirred 16 h at room temperature. To the reaction mixture was added 1 mL of water and the layers were separated. The organic layer was dried (Na2 SO4) and the solvent was removed with a rotary evaporator. The residue was purified by flash chromatography to give 0.33 g of the title compound as a yellow solid, m.p. 210°-212° C.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US4838925, 1989, A

45
[ 57683-71-3 ]
[ 2757-23-5 ]
o-Carboxymethylphenylsulfonyl isocyanate [ No CAS ]
[ 74222-95-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridine; thionyl chloride	I Production of o-Carboxymethylphenylsulfonyl isocyanate EXAMPLE I Production of o-Carboxymethylphenylsulfonyl isocyanate In a flask equipped with a stirrer, reflux condenser, and nitrogen bubbling apparatus were mixed 5 grams (g) (0.023 mole) o-carbomethoxyphenylsulfonamide, 50 milliliters (ml) (0.686 mole) thionyl chloride and 2 drops of pyridine. Then, 3 g (0.023 mole) chlorocarbonylsulfenyl chloride was added dropwise. The mixture was heated under reflux (100°-110° C.) under nitrogen, for 12 hours. The mixture was then cooled to room temperature and the thionyl chloride removed by rotary evaporation. A semi-liquid residue was obtained, which was analyzed by infrared spectroscopy, which indicated the presence of the desired isocyanate. The residue was distilled at 0.1 mm Hg and the product was taken off at 104°-111° C. There was obtained 4.4 g (79% yield) of the desired product, o-carbomethoxyphenylsulfonyl isocyanate. The structure was confirmed by comparison of the infrared spectrum of the product with that of the same compund prepared by reaction of the sulfonamide with phosgene.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US4485053, 1984, A

46
[ 57683-71-3 ]
[ 74-88-4 ]
[ 79672-26-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate	R.9 Compound i REFERENCE EXAMPLE 9 Compound i According to (1-2) described in Reference Example 1, methyl 2-(dimethylaminosulfonyl)benzoate was prepared from methyl 2-(aminosulfonyl)benzoate, methyl iodide and potassium carbonate, and then compound i was prepared according to (3-2) to (3-4) described in Reference Example 3. FAB-MS m/z: 231 [M+H]+ 1H-NMR (CDCl3+CD3OD) δ(ppm): 7.87 (1H, d, 7.9 Hz), 7.71 (1H, d, 7.6 Hz), 7.62 (1H, dd, 7.9, 7.3 Hz), 7.46 (1H, dd, 7.6, 7.3 Hz), 5.10 (2H, s), 2.81 (6H, s).

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - US6239168, 2001, B1

47
[ 613-91-2 ]
[ 57683-71-3 ]
[ 943963-84-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: acetophenone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

48
[ 946-89-4 ]
[ 57683-71-3 ]
[ 943963-90-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: cyclododecanone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

49
1-tetralone oxime [ No CAS ]
[ 57683-71-3 ]
[ 943963-87-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1-tetralone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

50
[ 2475-92-5 ]
[ 57683-71-3 ]
[ 943963-85-7 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 4-methoxyacetophenone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

51
[ 54951-36-9 ]
[ 57683-71-3 ]
[ 943963-88-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: 6-methoxy-1-tetralone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

52
3',4'-dimethoxyacetophenone oxime [ No CAS ]
[ 57683-71-3 ]
[ 943963-86-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: 3',4'-dimethoxyacetophenone oxime With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine In tetrahydrofuran; hexane at 0℃; Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane Heating; Further stages.;

Reference： [1]Grant, Bonnie J.; Kramp, Catherine R.; Knight, John D.; Meierhoefer, Michelle A.; Vella, Jarrett H.; Sober, Carolyn L.; Jones, Stephen S.; Metz, Clyde R.; Beam, Charles F.; Pennington, William T.; VanDerveer, Donald G.; Camper, N. Dwight [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 3, p. 627 - 632]

53
tert-butyl (E)-2-(1-phenylethylidene)hydrazine-1-carboxylate [ No CAS ]
[ 57683-71-3 ]
[ 1011502-54-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: tert-butyl (E)-2-(1-phenylethylidene)hydrazine-1-carboxylate; methyl 2-(aminosulfonyl)benzoate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0 - 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran Heating; Further stages.;