[ CAS No. 1516-37-6 ] {[proInfo.proName]}

Name: 1516-37-6|1-(2-Methoxyphenyl)thiourea|98%
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Quality Control of [ 1516-37-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1516-37-6 ]

CAS No. :	1516-37-6	MDL No. :	MFCD00022162
Formula :	C₈H₁₀N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HXCHZMHFZXNFIX-UHFFFAOYSA-N
M.W :	182.24	Pubchem ID :	722774
Synonyms :

Safety of [ 1516-37-6 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P501-P270-P264-P301+P310+P330-P405	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1516-37-6 ]

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

Upstream synthesis route of [ 1516-37-6 ]
Downstream synthetic route of [ 1516-37-6 ]

[ 1516-37-6 ] Synthesis Path-Upstream 1~2

1
[ 1516-37-6 ]
[ 5464-79-9 ]

Yield	Reaction Conditions	Operation in experiment
94.08%	at 40℃; for 17 h;	Compound 3 (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To which was added lithium bromide (2.6 g, 0.03 mol) at room temperature, and bromine (1 ml, 0.02 mol) was slowly added dropwise in an ice bath, and then heated to 40° C., stirred for 17 h. The reaction system was lowered to room temperature and kept for 2 h. The reaction solution was filtered by suction and washed with acetic acid, and dried in a vacuum oven to give a white solid 4 (3.5 g, 94.08percent).

Reference： [1] Patent: US2016/102066, 2016, A1, . Location in patent: Paragraph 0021; 0025; 0027
[2] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1136 - 1148
[3] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[4] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189[5] Chem.Abstr., 1941, p. 452
[6] Bulletin de la Societe Chimique de France, 1956, p. 684,688
[7] Heterocycles, 1980, vol. 14, # 8, p. 1145 - 1149
[8] Acta Poloniae Pharmaceutica - Drug Research, 2009, vol. 66, # 4, p. 387 - 392
[9] Patent: US2011/152246, 2011, A1, . Location in patent: Page/Page column 183
[10] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 6, p. 1351 - 1355
[11] Chemical Biology and Drug Design, 2016, p. 354 - 362
[12] Journal of Medicinal Chemistry, 2016, vol. 59, # 21, p. 9814 - 9824

2
[ 67-66-3 ]
[ 7726-95-6 ]
[ 1516-37-6 ]
[ 5464-79-9 ]

Reference： [1] Helvetica Chimica Acta, 1942, vol. 25, p. 515,519
[2] Yakugaku Zasshi, 1940, vol. 60, p. 462,473; dtsch. Ref. S. 184, 189[3] Chem.Abstr., 1941, p. 452

[ 1516-37-6 ] Synthesis Path-Downstream 1~88

1
[ 3288-04-8 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia
	With ammonia In dichloromethane at 0 - 20℃;
	With ammonia; water In ethyl acetate at 20℃;

Reference： [1]Hofmann,A. W. [Chemische Berichte, 1887, vol. 20, p. 1796]
[2]Yoo, Choong Leol; Yu, Gui Jun; Yang, Baoxue; Robins, Lori I.; Verkman; Kurth, Mark J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 8, p. 2610 - 2614]
[3]Location in patent: experimental part Nath, Jayashree; Patel, Bhisma K.; Jamir, Latonglila; Sinha, Upasana Bora; Satyanarayana [Green Chemistry, 2009, vol. 11, # 10, p. 1503 - 1506]

2
[ 1516-37-6 ]
[ 5464-79-9 ]

Yield	Reaction Conditions	Operation in experiment
94.08%	With bromine; acetic acid; lithium bromide; at 40℃; for 17h;	Compound 3 (3.76 g, 0.02 mol) was dissolved in acetic acid (36 ml). To which was added lithium bromide (2.6 g, 0.03 mol) at room temperature, and bromine (1 ml, 0.02 mol) was slowly added dropwise in an ice bath, and then heated to 40 C., stirred for 17 h. The reaction system was lowered to room temperature and kept for 2 h. The reaction solution was filtered by suction and washed with acetic acid, and dried in a vacuum oven to give a white solid 4 (3.5 g, 94.08%).
	With bromine; In chloroform; at 10℃; for 1h;Reflux;	General Procedure I-EJA solution of compound I-XVIa (10 g, 55 mmol) in chloroform (100 mL) was cooled to 10 C. and treated with a solution of bromine (8.8 g, 55 mmol) in chloroform (10 mL). The reaction was stirred at room temperature for 30 min. The resulting suspension was heated at reflux for 30 min. The precipitate was collected via filtration (washed with CH2Cl2) to give compound I-XVIb (5 g crude), which was used directly in the next step.

Reference： [1]Patent: US2016/102066,2016,A1 .Location in patent: Paragraph 0021; 0025; 0027
[2]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148
[3]Helvetica Chimica Acta,1942,vol. 25,p. 515,519
[4]Bulletin de la Societe Chimique de France,1956,p. 684,688
[5]Heterocycles,1980,vol. 14,p. 1145 - 1149
[6]Acta poloniae pharmaceutica,2009,vol. 66,p. 387 - 392
[7]Patent: US2011/152246,2011,A1 .Location in patent: Page/Page column 183
[8]Journal of Heterocyclic Chemistry,2011,vol. 48,p. 1351 - 1355
[9]Chemical Biology and Drug Design,2016,p. 354 - 362
[10]Journal of Medicinal Chemistry,2016,vol. 59,p. 9814 - 9824
[11]Archiv der Pharmazie,2019,vol. 352

3
[ 2379-60-4 ]
[ 1516-37-6 ]
[ 31102-87-1 ]
[ 31102-74-6 ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 859 - 862

4
[ 403-29-2 ]
[ 1516-37-6 ]
[ 78864-06-9 ]

Yield	Reaction Conditions	Operation in experiment
68.5%	In ethanol for 8h; Heating;
	In ethanol

Reference： [1]Pathak; Singh [Pharmazie, 1981, vol. 36, # 5, p. 331 - 332]
[2]Pathak; Singh [Journal of the Indian Chemical Society, 1979, vol. 56, # 10, p. 1010 - 1012]

5
[ 2958-87-4 ]
[ 1516-37-6 ]
[ 31102-90-6 ]
[ 31102-77-9 ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 859 - 862

6
[ 2958-87-4 ]
[ 1516-37-6 ]
[ 31102-77-9 ]

Reference： [1]Journal of the Indian Chemical Society,1970,vol. 47,p. 859 - 862

7
[ 16503-53-0 ]
[ 1516-37-6 ]
[ 109812-00-2 ]

Reference： [1]Journal of the Indian Chemical Society,1960,vol. 37,p. 435 - 436

8
[ 42981-08-8 ]
[ 1516-37-6 ]
[ 67241-25-2 ]

Reference： [1]Journal of Pharmaceutical Sciences,1978,vol. 67,p. 587 - 589

9
[ 350-27-6 ]
[ 1516-37-6 ]
[ 78864-20-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol for 8h; Heating;
	In ethanol

Reference： [1]Pathak; Singh [Pharmazie, 1981, vol. 36, # 5, p. 331 - 332]
[2]Pathak; Singh [Journal of the Indian Chemical Society, 1979, vol. 56, # 10, p. 1010 - 1012]

10
[ 49679-45-0 ]
[ 1516-37-6 ]
2-(2-Methoxy-phenylamino)-1-thia-3,9,10-triaza-anthracen-4-one [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 901 - 902

11
[ 21258-10-6 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrazine at 25℃; for 0.166667h;
90%	With sodium hydroxide at 90 - 95℃; for 0.133333h;
75%	With sodium hydroxide at 100℃;

	With sodium hydroxide In tetrahydrofuran for 3h; Heating;
	With sodium hydroxide
	With water; sodium hydroxide at 70℃; for 0.333333h;
	With sodium hydroxide In tetrahydrofuran; water at 100℃; for 1h;	5.1.3. General procedure for the synthesis of N-substituted thioureas (E, Scheme 1) General procedure: A solution of N-aryl-N'-benzoylthiourea (D) in aqueous sodium hydroxide (2 M)/THF (1:1) was heated to 100 °C for 1 h. The precipitating solid N-substituted thiourea (E) was collected and washed with H2O.30
	With water; sodium hydroxide In ethanol for 1h; Reflux;	General procedure: A solution of benzoyl chloride 4 (0.14 g, 1 mmol) and ammonium thiocyanate 5 (0.08 g, 1 mmol) in acetone (8 mL)was heated under reflux for 10-20 min to give intermediate 6. After completion of reaction (checked by TLC), aniline derivative 7 (0.09 or 0.12 g, 1 mmol) was added to the reaction mixture and the reaction was continued for further 3 h.After that it was poured into the crushed ice and the precipitate was filtered off to give compound 8 (70%) [33]. Next, a mixture of compound 8 (0.26 or 0.29 g, 1 mmol) and NaOH(aq, 10%, 1 mL) in ethanol (8 mL) was heated under reflux conditions for 1 h. After completion of reaction, the mixture was poured into the crushed ice and the precipitate was filtered off to give compound 9 (83%) [34]. Finally, a mixture of compound 9 (0.15 or 0.18 g, 1 mmol), ethyl 2-bromoacetate 10 (0.17 g, 1 mmol), and NEt3 (0.10 g, 1mmol) in ethanol (8 mL) was heated at reflux for 2 h. After completion of reaction, the mixture was poured into the crushed ice and the precipitate was filtered off to afford 2-arylthiazol-4(5H)-one derivative 1 (77%) [35]. A solution of compound 1 (0.19 or 0.22 g, 1 mmol), aldehyde derivative 2(1 mmol), and piperidine (0.08 g, 1 mmol) in ethanol (8 mL)was heated at reflux for 1 h. After completion of reaction(checked by TLC), the reaction mixture was cooled to room temperature, the precipitate was filtered off, and washed with cold ethanol to give pure product 3.
	With ammonium hydroxide In methanol Reflux;
	With sodium hydroxide In water for 1h; Reflux;

Reference： [1]Kodomari, Mitsuo; Suzuki, Masato; Tanigawa, Keiko; Aoyama, Tadashi [Tetrahedron Letters, 2005, vol. 46, # 35, p. 5841 - 5843]
[2]Rasmussen, C. R.; Villani, F. J.; Weaner, L. E.; Reynolds, B. E.; Hood, A. R.; et al. [Synthesis, 1988, # 6, p. 456 - 459]
[3]Gupta, K. A.; Saxena, Anil K.; Jain, Padam C. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 228 - 233]
[4]Shearer, Barry G.; Lee, Shuliang; Oplinger, Jeffrey A.; Frick, Lloyd W.; Garvey, Edward P.; Furfine, Eric S. [Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1901 - 1905]
[5]Holla, B. Shivarama; Malini; Rao, B. Sooryanarayana; Sarojini; Kumari, N. Suchetha [European Journal of Medicinal Chemistry, 2003, vol. 38, # 3, p. 313 - 318]
[6]Thanigaimalai; Le Hoang, Tuan Anh; Lee, Ki-Cheul; Bang, Seong-Cheol; Sharma, Vinay K.; Yun, Cheong-Yong; Roh, Eunmiri; Hwang, Bang-Yeon; Kim, Youngsoo; Jung, Sang-Hun [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2991 - 2993]
[7]Vogt, Dominik; Weber, Julia; Ihlefeld, Katja; Brüggerhoff, Astrid; Proschak, Ewgenij; Stark, Holger [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 19, p. 5354 - 5367]
[8]Mahdavi, Mohammad; Saeedi, Mina; Nadri, Hamid; Eghtedari, Mohammad; Gholizadeh, Sama; Hariri, Roshanak; Akbarzadeh, Tahmineh [Letters in Organic Chemistry, 2017, vol. 14, # 3, p. 186 - 191]
[9]Ye, Jiao; Xiao, Meng-Wu; Xie, Xuan-Qing; Qiu, Shen-Yi; Dai, Ming-Chong; Li, Wan; Shen, Fang; Hu, Ai-Xi [Journal of the Chinese Chemical Society, 2015, vol. 62, # 7, p. 627 - 631]
[10]Ropponen, Henni-Karoliina; Bader, Chantal D.; Diamanti, Eleonora; Illarionov, Boris; Rottmann, Matthias; Fischer, Markus; Witschel, Matthias; Müller, Rolf; Hirsch, Anna K. H. [ChemMedChem, 2021, vol. 16, # 13, p. 2089 - 2093]

12
[ 1147550-11-5 ]
[ 90-04-0 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
28.74%	Stage #1: ammonium thiocyanate; 2-methoxy-phenylamine With hydrogenchloride In water monomer for 1h; Heating; Stage #2: Heating;	General procedure for the synthesis of aryl thiourea(1a-i) General procedure: To a suspension of (0.30 mol) of aryl amine in 100 mL ofwarm water, concentrated hydrochloric acid (HCl) (0.33mol, 9.16 mL) was added with stirring. The resulting solutionwas placed in a large porcelain evaporating dish,ammonium thiocyanate (0.3 mol, 8.33 g) was added and themixture was heated on a steam bath for 1 h. The liquid, fromwhich a mass of large needles of aryl amine thiocyanateseparated, was allowed to cool, set aside at room temperaturefor 1 h and then evaporated slowly to dryness over aperiod of 2-3 hrs. The crystalline residue was crushedfinely, 100 mL water was added, and again the mixture wasevaporated slowly. The dry grayish white residual powderwas heated finally on a steam bath for 4-5 hrs. The resultingmixture of crude substituted phenylthiourea and ammoniumchloride was powdered finely and suspended in 100 mL ofwater. The mixture was warmed slowly to 70 °C with stirring,and then allowed to cool to 35 °C and the solid wasfiltered with suction. The crude material was dissolved inabsolute ethanol, the solution boiled with decolourizingcarbon for a few minutes and then filtered. The whitecrystalline mass of substituted phenylthiourea, whichseparated on cooling and standing, was separated by filtration,was washed with light petroleum ether and dried.Thin layer chromatography was carried out on precoatedsilica plates, using the solvent system methanol: chloroform (1:9). Physical and spectral analysis confirmed the formationof the corresponding thiourea (Rabjohn, 2005).
24%	Stage #1: ammonium thiocyanate; 2-methoxy-phenylamine With hydrogenchloride In water monomer at 100℃; for 16h; Stage #2: With ammonia In water monomer at 5℃; for 2h;	I.I-XVI.I-EI Example I-XVIPreparation of Compound 320General Procedure I-EIAmmonium thiocyanate (NH4SCN; 3.37 g, 44.3 mmol) was added to a stirred solution of o-anisidine (5.00 g, 44.3 mmol) in aq. HCl (1 M, 45 mL) at 100° C. and the solution stirred at 100° C. for 16 hrs. The solution was diluted with water (60 mL) and the pH value was adjusted to 8 with aqueous ammonia and the mixture was stirred at 5° C. for 2 hrs. The precipitate was filtered, washed with water (5 mL) and ether (5 mL), and dried. The crude solid was purified by column chromatography (petroleum ether/ethyl acetate=4/1), to give compound I-XVIa (1.93 g, yield 24%) as a white powder. MS (ESI) m/z (M+H)+ 183.3.
24%	With hydrogenchloride In water monomer at 100℃; for 16h;	1-68 Example 1-68 7V-(2-Methoxyphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (109). [0322] 2-Methoxyphenylthiourea (108). NH4SCN (3.37 g, 44.3 mmol) was added to a stirred solution of o-anisidine (5.00 g, 44.3 mmol) in 1 M HCl (45 mL) at 100 0C and the solution stirred at 100 0C for 16 h. The solution was diluted with water (60 mL) and the pH adjusted to 8 with aqueous NH3 and the mixture at 5 0C for 2 h. The precipitate was filtered, washed with water (5 mL), washed with ether (5 mL), and dried. The crude solid was purified by column chromatography, eluting with 40% EtO Ac/pet, ether, to give thiourea 108 (1.93 g, 24%) as a white powder: mp (EtO Ac/pet, ether) 151-153 0C [lit. (Rasmussen, C. R. et al, Synthesis 1988, 456) mp (MeOH) 153-155 0C]; 1H NMR δ 8.99 (s, 1 H, NH), 7.81 (br d, J = 7.7 Hz, 1 H, H-3), 7.40 br s, 2 H, NH2), 7.13 (ddd, J= 8.2, 7.6, 1.6 Hz, 1 H, H- 5), 7.04 ( dd, J= 8.2, 1.3 Hz, 1 H, H-6), 6.90 (ddd, J= 7.7, 7.6, 1.3 Hz, 1 H, H-4), 3.81 (s, 3 H, OCH3); MS m/z 183.3 (MH+, 100%).

	In water monomer for 4h; Heating;
	With hydrogenchloride In water monomer
	In water monomer
	With hydrogenchloride In water monomer Heating;
	With benzoyl chloride In acetone
	Stage #1: ammonium thiocyanate With substituted benzoyl chloride In acetone at 60℃; for 0.166667h; Stage #2: 2-methoxy-phenylamine In acetone at 60℃; for 1h;	Synthesis of Substituted Phenylthiourea(5) General procedure: To a solution of substituted benzoyl chloride (8 mL, 68.73 mmol) in acetone (15 mL) was added ammonium thiocyanate (5.93 g, 77.89 mmol) at room temperature. After the reaction solution was stirred at 60 C for 10 min, substituted aniline (45.92 mmol) in acetone (5 mL) was added slowly. The mixture was stirred at 60 C for 1 h and then extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and filtered. The solvent was evaporated under reduced pressure, and the residual mixture was poured into diethyl ether to afford white solids. The solid was stirred in 10% sodium hydroxide solution at 80 C for 1 h and neutralized by 4 N hydrogen chloride to yield a solid. The crude solid was filtered, washed with 50% methanol, and dried by reduced pressure to give a white solid (3,5-dimethoxyphenyl)thiourea. Yield 86%; 1H NMR (300 MHz, DMSO-d6) δ: 8.71 (brs,1H), 6.40 (d, J = 2.2 Hz, 1H), 6.37(d, J = 2.2 Hz, 2H), 6.15 (brs, 2H), 3.80 (s, 6H).
	With hydrogenchloride
	Stage #1: ammonium thiocyanate With benzoyl chloride In acetone at 20℃; Stage #2: 2-methoxy-phenylamine In ethyl acetate; acetone at 20℃;
	With hydrogenchloride In water monomer

Reference： [1]Diwakar, Kirti; Sonar, Pankaj Kumar; Mishra, Mudita; Tripathi, Avinash C.; Saraf, Shailendra K. [Medicinal Chemistry Research, 2016, vol. 25, # 11, p. 2631 - 2642]
[2]Current Patent Assignee: BEIJING KAWIN TECHNOLOGY - US2011/152246, 2011, A1 Location in patent: Page/Page column 181-183
[3]Current Patent Assignee: STANFORD UNIVERSITY - WO2009/114552, 2009, A1 Location in patent: Page/Page column 138
[4]Gupta, R. R.; Ojha, K. G.; Kalwania, G. S.; Kumar, M. [Heterocycles, 1980, vol. 14, # 8, p. 1145 - 1149]
[5]Location in patent: body text Yar, Mohammad Shahar; Ansari, Zaheen Hasan [Acta poloniae pharmaceutica, 2009, vol. 66, # 4, p. 387 - 392]
[6]Location in patent: scheme or table Kumar; Sharma, Kshitija; Samarth; Kumar [European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4467 - 4472]
[7]Location in patent: experimental part Siddiqui, Nadeem; Shaquiquzzaman; Rahman, Mujeeb Ur; Arshad, M. Faiz; Waquar, Ahsan; Alam, M. Shamsher; Sharique, Ahmed [Acta poloniae pharmaceutica, 2010, vol. 67, # 3, p. 239 - 246] Location in patent: experimental part Kabra, Uma; Chopde, Chandrabhan; Wadodkar, Sudhir [Journal of Heterocyclic Chemistry, 2011, vol. 48, # 6, p. 1351 - 1355] Location in patent: experimental part Siddiqui, Nadeem; Ahsan, Waquar [Medicinal Chemistry Research, 2011, vol. 20, # 2, p. 261 - 268]
[8]Location in patent: body text Acharjee, Satarupa; Bothara, Kailash G.; Bhandari, Shashikant V.; Maity, Tapan K. [Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 705 - 713]
[9]Kim, Hee Sook; Shin, Min Jae; Lee, Byungho; Oh, Kwang-Seok; Choo, Hyunah; Pae, Ae Nim; Roh, Eun Joo; Nam, Ghilsoo [Bulletin of the Korean Chemical Society, 2015, vol. 36, # 11, p. 2621 - 2626]
[10]Kharbanda, Chetna; Alam, Mohammad Sarwar; Hamid, Hinna; Javed, Kalim; Bano, Sameena; Ali, Yakub; Dhulap, Abhijeet; Alam, Perwez; Pasha, M. A. Qadar [Chemical Biology and Drug Design, 2016, p. 354 - 362]
[11]Feng, Yian; Zou, Minming; Song, Runjiang; Shao, Xusheng; Li, Zhong; Qian, Xuhong [Journal of Organic Chemistry, 2016, vol. 81, # 21, p. 10321 - 10327]
[12]Korpe, Gajanan V.; Mopari, Anuja M. [Asian Journal of Chemistry, 2022, vol. 34, # 5, p. 1220 - 1224]

13
[ 123-54-6 ]
[ 1516-37-6 ]
[ 75276-65-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride In ethanol for 3h; Heating;

Reference： [1]Kashima, Choji; Katoh, Akira [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1599 - 1602]

14
[ 58303-62-1 ]
[ 1516-37-6 ]
[ 122351-45-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetic acid for 0.666667h; Heating;

Reference： [1]Andreichikov, Yu. S.; Nekrasov, D. D.; Rudenko, M. A.; Nalimova, Yu. A. [Chemistry of Heterocyclic Compounds, 1988, vol. 24, # 10, p. 1172 - 1174][Khimiya Geterotsiklicheskikh Soedinenii, 1988, vol. 24, # 10, p. 1411 - 1413]

15
[ 122886-85-5 ]
[ 1516-37-6 ]
4-{4-(4-Methoxy-phenylamino)-6-[3-(2-methoxy-phenyl)-thioureido]-[1,3,5]triazin-2-ylamino}-N-(6-methoxy-pyridazin-3-yl)-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In acetone at 90℃; for 3h;

Reference： [1]Desai; Mistry [Journal of the Indian Chemical Society, 1988, vol. 65, # 11, p. 806 - 807]

16
[ 1516-37-6 ]
[ 55991-69-0 ]
[ 122351-46-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetic acid for 0.666667h; Heating;

17
[ 1516-37-6 ]
[ 74-88-4 ]
[ 35677-69-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	In methanol for 1h; Ambient temperature;

Reference： [1]Rasmussen, C. R.; Villani, F. J.; Reynolds, B. E.; Plampin, J. N.; Hood, A. R.; et al. [Synthesis, 1988, # 6, p. 460 - 466]

18
[ 175856-50-5 ]
[ 1516-37-6 ]
2-Imino-7-[(E)-2-methoxy-phenylimino]-1,6-dithia-3,8-diaza-spiro[4.4]nonane-4,9-dione [ No CAS ]
2-Imino-5-(2-methoxy-phenylcarbamimidoylsulfanyl)-4-oxo-thiazolidine-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 10.8% 2: 31%	With sodium acetate In ethanol at 70℃; for 0.666667h;
1: 31% 2: 10.8%	With sodium acetate In ethanol at 70℃; for 0.666667h;

Reference： [1]Chande, Madhukar S.; Ambhaikar, Shireesh B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 373 - 376]
[2]Chande, Madhukar S.; Ambhaikar, Shireesh B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 373 - 376]

19
[ 175856-51-6 ]
[ 1516-37-6 ]
2-[(E)-2-Methoxy-phenylimino]-7-[(E)-phenylimino]-1,6-dithia-3,8-diaza-spiro[4.4]nonane-4,9-dione [ No CAS ]
5-(2-Methoxy-phenylcarbamimidoylsulfanyl)-4-oxo-2-[(E)-phenylimino]-thiazolidine-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 18% 2: 35%	With sodium acetate In ethanol at 70℃; for 0.666667h;
1: 35% 2: 18%	With sodium acetate In ethanol at 70℃; for 0.666667h;

20
[ 175856-52-7 ]
[ 1516-37-6 ]
2-[(E)-2-Methoxy-phenylimino]-7-[(E)-p-tolylimino]-1,6-dithia-3,8-diaza-spiro[4.4]nonane-4,9-dione [ No CAS ]
5-(2-Methoxy-phenylcarbamimidoylsulfanyl)-4-oxo-2-[(E)-p-tolylimino]-thiazolidine-5-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 8.7% 2: 60.6%	With sodium acetate In ethanol at 70℃; for 0.666667h;

Reference： [1]Chande, Madhukar S.; Ambhaikar, Shireesh B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 4, p. 373 - 376]

21
[ 105-56-6 ]
[ 1516-37-6 ]
[ 180028-94-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride In 1,4-dioxane at 0 - 5℃; for 17h; Heating;

Reference： [1]Shishoo; Jain; Jain; Shah; Ravikumar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 662 - 668]

22
[ 81918-04-9 ]
[ 1516-37-6 ]
[ 260243-58-1 ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In ethanol for 3h; Heating;

Reference： [1]Chande, Madhukar S.; Bhat, Udayashankar S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 932 - 937]

23
[ 67-66-3 ]
[ 7726-95-6 ]
[ 1516-37-6 ]
[ 5464-79-9 ]

Reference： [1]Helvetica Chimica Acta,1942,vol. 25,p. 515,519

24
[ 631-22-1 ]
[ 2231-57-4 ]
[ 1516-37-6 ]
7-Hydrazino-2-[(E)-2-methoxy-phenylimino]-1,6-dithia-3,8,9-triaza-spiro[4.5]dec-7-ene-4,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: diethyl dibromomalonate; 1-(2-methoxyphenyl)thiourea With potassium fluoride In N,N-dimethyl-formamide for 2h; Heating; Stage #2: Thiocarbohydrazide In N,N-dimethyl-formamide for 1h; Heating;

Reference： [1]Chande, Madhukar S.; Pankhi, Mohd Aslam; Sugdare, Vijay V.; Ambhaikar, Shireesh B. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 925 - 931]

25
[ 1516-37-6 ]
[ 286841-45-0 ]
2-[(E)-2-Methoxy-phenylimino]-9-methyl-7-oxa-1-thia-3,8-diaza-spiro[4.4]non-8-ene-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium fluoride In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Chande; Bhat [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 1, p. 68 - 70]

26
[ 1516-37-6 ]
[ 286841-49-4 ]
2-[(E)-2-Methoxy-phenylimino]-9-phenyl-7-oxa-1-thia-3,8-diaza-spiro[4.4]non-8-ene-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium fluoride In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Chande; Bhat [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 1, p. 68 - 70]

27
[ 93-91-4 ]
[ 1516-37-6 ]
1-(o-methoxyphenyl)-4-methyl-6-phenyl-2[1H]-pyrimidinethione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.1%	With hydrogenchloride In ethanol for 6h; Heating;
	With hydrogenchloride

Reference： [1]Zylewska, Alicja; Tejchman, Waldemar; Korohoda, Maria J.; Zylewski, Marek [Heterocycles, 2003, vol. 60, # 12, p. 2749 - 2760]
[2]Żesławska, Ewa; Korona-Głowniak, Izabela; Nitek, Wojciech; Tejchman, Waldemar [Acta Crystallographica Section C: Structural Chemistry, 2020, vol. 76, p. 359 - 366]

28
[ 851019-94-8 ]
[ 1516-37-6 ]
1-(2-methoxy-phenyl)-3-[4-(2-methyl-5-nitro-imidazol-1-yl)-6-(4-methyl-2-oxo-2<i>H</i>-chromen-7-yloxy)-[1,3,5]triazin-2-yl]-thiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium hydrogencarbonate In acetone for 4h; Heating;

Reference： [1]Patel; Chikhalia; Desai [Journal of the Indian Chemical Society, 2005, vol. 82, # 1, p. 83 - 85]

29
[ 916139-91-8 ]
[ 1516-37-6 ]
2-[(Z)-2-Methoxy-phenylimino]-9-methyl-7-phenyl-1-thia-3,7,8-triaza-spiro[4.4]non-8-ene-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium fluoride In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Chande, Madhukar S.; Bhat, Udayashankar S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1041 - 1047]

30
[ 916139-92-9 ]
[ 1516-37-6 ]
2-[(Z)-2-Methoxy-phenylimino]-7,9-diphenyl-1-thia-3,7,8-triaza-spiro[4.4]non-8-ene-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium fluoride In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Chande, Madhukar S.; Bhat, Udayashankar S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1041 - 1047]

31
[ 916139-93-0 ]
[ 1516-37-6 ]
2-[(Z)-2-Methoxy-phenylimino]-9-(4-nitro-phenyl)-7-phenyl-1-thia-3,7,8-triaza-spiro[4.4]non-8-ene-4,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium fluoride In N,N-dimethyl-formamide for 1.5h; Heating;

Reference： [1]Chande, Madhukar S.; Bhat, Udayashankar S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 4, p. 1041 - 1047]

32
[ 90-04-0 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 1 h / 25 °C 2: 96 percent / NH₂NH₂ / 0.17 h / 25 °C
	Multi-step reaction with 2 steps 1: 88 percent / acetone / 0.5 h / Heating 2: 90 percent / 5percent aq. NaOH / 0.13 h / 90 - 95 °C
	Multi-step reaction with 2 steps 1: 91 percent / benzene 2: 75 percent / 2,5 N NaOH / 100 °C

	Multi-step reaction with 2 steps 1: acetone / Reflux 2: ammonium hydroxide / methanol / Reflux
	Multi-step reaction with 2 steps 1: acetone / 1.5 h / Reflux 2: sodium hydroxide / water / 1 h / Reflux

33
[ 90-04-0 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetone / Ambient temperature 2: 2.0 N aq. NaOH / tetrahydrofuran / 3 h / Heating

Reference： [1]Shearer, Barry G.; Lee, Shuliang; Oplinger, Jeffrey A.; Frick, Lloyd W.; Garvey, Edward P.; Furfine, Eric S. [Journal of Medicinal Chemistry, 1997, vol. 40, # 12, p. 1901 - 1905]

34
[ 1226-64-8 ]
[ 1516-37-6 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 1796

35
[ 1516-37-6 ]
[ 16238-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: methanol 2: H₂ / Pd-C / ethyl acetate

Reference： [1]Lown,J.W.; Ma,J.C.N. [Canadian Journal of Chemistry, 1967, vol. 45, p. 939 - 951]

36
[ 1516-37-6 ]
[ 237383-00-5 ]
methyl 4-{2-[(3-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		158.a EXAMPLE 158 a) Methyl 4-{2-[(3-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (53.3 mg, 0.17 mmol) was allowed to react with 2-methoxy phenyl thiourea (34.5 mg) as described in Example 154, step (a), to give 61 mg (76% yield) of methyl 4-{2-[(3-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ2.67 (s, 3 H), 3.78 (s, 3 H), 3.83 (s, 3 H), 6.53 (d, 1 H, J=6.8 Hz), 7.13-7.24 (m, 2 H), 7.29 (s, 3 H), 7.59 (m, 1 H), 8.16 (s, 3 H), 10.32 (s, 1 H); Mass Spectrum (ESI) m/z calcd. for C17H16N2O3S3, 392.52 (M+H), found 393.2.
76%		158.a EXAMPLE 158 a) Methyl 4-{2-[(3-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide Methyl 4-(2-bromoacetyl)-5-methylthiothiophene-2-carboxylate (53.3 mg, 0.17 mmol) was allowed to react with 2-methoxy phenyl thiourea (34.5 mg) as described in Example 154, step (a), to give 61 mg (76% yield) of methyl 4-{2-[(3-methoxyphenyl)amino](1,3-thiazol-4-yl)}-5-methylthiothiophene-2-carboxylate hydrobromide. 1H NMR (DMSO-d6, 300 MHz) δ 2.67 (s, 3H), 3.78 (s, 3H), 3.83 (s, 3H), 6.53 (d, 1H, J=6.8 Hz), 7.13-7.24 (m, 2H), 7.29 (s, 3H), 7.59 (m, 1H), 8.16 (s, 3H), 10.32 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C17H16N2O3S3, 392.52 (M+H), found 393.2.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2002/37915, 2002, A1
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US6291514, 2001, B1

37
[ 333-20-0 ]
[ 90-04-0 ]
[ 1226-64-8 ]
[ 1516-37-6 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 3508 - 3515

38
[ 1516-37-6 ]
[ 110605-13-5 ]

Yield	Reaction Conditions	Operation in experiment
27.05%	With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 3h;	General procedure for the synthesis of (5-imino-4-phenyl-4,5-dihydro-[1,2,4] thiadiazol-3-yl)-phenyl-aminederivatives (2a-i) General procedure: The substituted phenylthiourea (4.18 × 10-3 mol) wascompletely dissolved in aqueous sodium hydroxide (2N, 30mL, 4 × 10-2 mol) at 0 °C. Hydrogen peroxide (30 %, 0.13mL, 5.51 × 10-3 mol) was then added drop-wise to thereaction mixture. The mixture was stirred for 3 hrs. at thesame temperature and then it was acidified with concentratedHCl to get a pH of 4.5. The resulting colourlesssolid was separated and collected by filtration. It wasrecrystallized from ethanol to give the pure compound (Choet al., 1991). TLC was carried out on precoated silica plateusing the slovent system, methanol: chloroform (1:9).
	With bromine; sodium acetate; acetic acid at 20 - 40℃;

Reference： [1]Diwakar, Kirti; Sonar, Pankaj Kumar; Mishra, Mudita; Tripathi, Avinash C.; Saraf, Shailendra K. [Medicinal Chemistry Research, 2016, vol. 25, # 11, p. 2631 - 2642]
[2]Thiel, Oliver R.; Bernard, Charles; King, Tony; Dilmeghani-Seran, Mina; Bostick, Tracy; Larsen, Robert D.; Faul, Margaret M. [Journal of Organic Chemistry, 2008, vol. 73, # 9, p. 3508 - 3515]

39
ammonium thiocyanate [ No CAS ]
[ 90-04-0 ]
[ 1516-37-6 ]

Yield	Reaction Conditions	Operation in experiment
24%	With hydrogenchloride In water at 100℃; for 16h;
	With hydrogenchloride at 80℃; for 12h;

Reference： [1]Hay, Michael P.; Turcotte, Sandra; Flanagan, Jack U.; Bonnet, Muriel; Chan, Denise A.; Sutphin, Patrick D.; Nguyen, Phuong; Giaccia, Amato J.; Denny, William A. [Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797]
[2]Zhou, Hongyu; Wu, Shuhong; Zhai, Shumei; Liu, Aifeng; Sun, Ying; Li, Rongshi; Zhang, Ying; Ekins, Sean; Swaan, Peter W.; Fang, Bingliang; Zhang, Bin; Yan, Bing [Journal of Medicinal Chemistry, 2008, vol. 51, # 5, p. 1242 - 1251]

40
[ 105-39-5 ]
[ 1516-37-6 ]
[ 1253116-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 60℃; for 6h;

Reference： [1]Zhou, Hongyu; Wu, Shuhong; Zhai, Shumei; Liu, Aifeng; Sun, Ying; Li, Rongshi; Zhang, Ying; Ekins, Sean; Swaan, Peter W.; Fang, Bingliang; Zhang, Bin; Yan, Bing [Journal of Medicinal Chemistry, 2008, vol. 51, # 5, p. 1242 - 1251]

41
[ 1516-37-6 ]
[ 65195-61-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ammonium hydroxide; di(acetyloxy)iodobenzene In acetonitrile at 20℃; for 4.16667h; Cooling with ice;	3.i Preparation of N-(2-Methoxyphenyl)cyanamide (2): Aqueous ammonia (25%, 90 mL) was added to a stirred and ice-cooled suspension of 1-(2-methoxyphenyl)thiourea (1) (5.00 g, 27.44 mmol) in acetonitrile (90 mL). Diacetoxyiodobenzene (10.60 g, 32.92 mmol) was added portion-wise over a period of 10 min. The reaction mixture was stirred at room temperature for 4 h, and the precipitated sulfur was filtered. The filtrate was concentrated (until ½ of volume) and extracted with ethyl acetate (320 mL). The ethyl acetate layer was washed with water (230 mL) and then with brine (50 mL). The organic layer was dried over anhydrous solid Na2SO4, filtered and the filtrate concentrated under reduced pressure. The resultant residue was purified by flash column chromatography using petroleum ether/ethyl ether (1:1) to give the N-(2-methoxyphenyl)-cyanamide (2) (3.33 g, 82% yield). 300 MHz 1H-NMR (CDCl3, ppm): 7.08 (ddd, J=7.5, 1.9, 0.5 Hz, 1H) 7.04 (ddd, J=7.5, 7.5, 1.9 Hz) 6.98 (ddd, J=7.5, 7.5, 1.7 Hz) 6.88 (dd, J=7.5, 1.7 Hz) 6.26 (s, 1H) 3.88 (s, 3H). ESI-MS (m/z): 149 [M+H]+.
82%	With ammonium hydroxide; [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 4.16667h; Cooling with ice;	3.i Preparation of N-(2-Methoxyphenyl)cyanamide (2) Aqueous ammonia (25%, 90 mL) was added to a stirred and ice-cooled suspension of l-(2-methoxyphenyl)thiourea (1) (5.00 g, 27.44 mmol) in acetonitrile (90 mL). Diacetoxyiodobenzene (10.60 g, 32.92 mmol) was added portion-wise over a period of 10 min. The reaction mixture was stirred at room temperature for 4 h, and the precipitated sulfur was filtered. The filtrate was concentrated to approximately 50% of its initial volume and extracted with ethyl acetate (3 x 20 mL). The ethyl acetate layer was washed with water (2 x 30 mL) and then with brine (50 mL). The organic layer was dried over anhydrous solid Na2SC>4, filtered and the filtrate concentrated under reduced pressure. The resultant residue was purified by flash column chromatography using petroleum ether/ethyl ether (1 : 1) to give the N-(2-methoxyphenyl)-cyanamide (2) (3.33 g, 82 % yield). 300 MHz ^-NMR (CDCI3, ppm): 7.08 (ddd, J=7.5, 1.9, 0.5 Hz, 1H) 7.04 (ddd, J=7.5, 7.5, 1.9 Hz) 6.98 (ddd, J=7.5, 7.5, 1.7 Hz) 6.88 (dd, J=7.5, 1.7 Hz) 6.26 (s, 1H) 3.88 (s, 3H). ESI-MS (m/z): 149 [M+H]+.
	With [bis(acetoxy)iodo]benzene; ammonia In water; acetonitrile for 0.416667h; Cooling with ice;

With iodine; triethylamine In water; ethyl acetate

Reference： [1]Current Patent Assignee: ACADIA PHARMACEUTICALS INC - US2020/246318, 2020, A1 Location in patent: Paragraph 0146; 0147; 0148
[2]Current Patent Assignee: ACADIA PHARMACEUTICALS INC - WO2020/231496, 2020, A1 Location in patent: Page/Page column 24-25
[3]Location in patent: experimental part Ghosh, Harisadhan; Yella, Ramesh; Ali, Abdur Rezzak; Sahoo, Santosh K.; Patel, Bhisma K. [Tetrahedron Letters, 2009, vol. 50, # 20, p. 2407 - 2410]
[4]Location in patent: experimental part Nath, Jayashree; Patel, Bhisma K.; Jamir, Latonglila; Sinha, Upasana Bora; Satyanarayana [Green Chemistry, 2009, vol. 11, # 10, p. 1503 - 1506]

42
[ 5349-17-7 ]
[ 1516-37-6 ]
[ 420103-37-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		[0323] 7V-(2-Methoxyphenyl]-4-(4-pyridinyl)-l,3-thiazol-2-amine (109). A mixture of bromoketone hydrobromide 1 (0.29 g, 1.1 mmol) and 2- methoxyphenylthiourea (108) (0.19 g, 1.1 mmol) in EtOH (15 mL) was stirred at reflux temperature for 1 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (50-100%) of EtO Ac/pet, ether, to give amine 109 (0.28 g, 93%) as a cream powder: mp (EtOAc/pet. ether) 190-191 0C; 1H NMR delta 9.67 (br s, 1 H, NH), 8.60 (dd, J= 4.5, 1.6 Hz, 2 H, H-2', H-6'), 8.48 (br d, J= 7.7 Hz, 1 H, H-3"), 7.83 (dd, J= 4.5, 1.6 Hz, 2 H, H-3', H-5'), 7.66 (s, 1 H, H-5), 6.97-7.00 (m, 3 H, H-4", H-5", H-6"), 3.87 (s, 3 H, OCH3); 13C NMR delta 164.0, 150.0 (2), 148.0, 147.2, 141.0, 129.0, 122.1, 120.6, 119.7 (2), 118.2, 110.9, 108.0, 55.6; MS m/z 284.5 (MH+, 100%). Anal, calcd for Ci5Hi3N3OS: C, 63.58; H, 4.62; N, 14.83. Found: C, 63.63; H, 4.64; N, 14.77%.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 787 - 797
[2]Patent: WO2009/114552,2009,A1 .Location in patent: Page/Page column 139

43
[ 1226644-48-9 ]
[ 1516-37-6 ]
[ 1226644-65-0 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydroxide In water; acetone at 85 - 90℃; for 2h;

Reference： [1]Location in patent: experimental part Sareen, Vineeta; Khatri, Vineeta; Jain, Prakash; Sharma, Kanti [Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 1, p. 140 - 146]

44
[ 1516-37-6 ]
[ 40207-02-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In ethanol for 16h; Reflux;
	With hydrazine hydrate In ethanol for 16h; Reflux;

Reference： [1]Location in patent: experimental part Siddiqui, Nadeem; Ahsan, Waquar [European Journal of Medicinal Chemistry, 2010, vol. 45, # 4, p. 1536 - 1543]
[2]Location in patent: experimental part Siddiqui, Nadeem; Ahsan, Waquar [Medicinal Chemistry Research, 2011, vol. 20, # 2, p. 261 - 268]

45
[ 1227465-11-3 ]
[ 1516-37-6 ]
[ 1227465-06-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium hydrogencarbonate In 1,4-dioxane; water at 80 - 100℃; for 4h;

Reference： [1]Location in patent: experimental part Patel, Amit C.; Mahajan, Dharmesh H.; Chikhalia, Kishor H. [Phosphorus, Sulfur and Silicon and the Related Elements, 2010, vol. 185, # 2, p. 368 - 376]

46
[ 79-04-9 ]
[ 1516-37-6 ]
1-(2-methoxyphenyl)-2-thiohydantoin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In PEG 400 at 80℃; for 2h;

Reference： [1]Location in patent: experimental part Kidwai, Mazaahir; Jahan, Anwar; Bhatnagar, Divya [Journal of Sulfur Chemistry, 2010, vol. 31, # 3, p. 161 - 167]

47
[ 1516-37-6 ]
[ 1312610-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromine / chloroform / 1 h / 10 °C / Reflux 2: tert.-butylnitrite / N,N-dimethyl-formamide / 1 h / 60 °C 3: aluminum (III) chloride / carbon disulfide / 1.5 h / Reflux