828-81-9|5-(2-Chlorophenyl)-1,3,4-thiadiazol-2-amine| Ambeed

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Quality Control of [ 828-81-9 ] Purity: 95% SDS Specification

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Product Details of [ 828-81-9 ]

CAS No. :	828-81-9
Formula :	C₈H₆ClN₃S
M.W :	211.67
SMILES Code :	NC1=NN=C(C2=CC=CC=C2Cl)S1
MDL No. :	MFCD00548482
InChI Key :	JKSGNHRIXMYPIO-UHFFFAOYSA-N
Pubchem ID :	554211

Safety of [ 828-81-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of [ 828-81-9 ]

* 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 [ 828-81-9 ]

[ 828-81-9 ] Synthesis Path-Downstream 1~35

1
[ 79-36-7 ]
[ 828-81-9 ]
[ 18199-98-9 ]

References: [1]Pharmazie,1967,vol. 22,p. 434 - 436.

2
[ 828-81-9 ]
[ 100-47-0 ]
[ 70038-86-7 ]

References: [1]Journal of the Indian Chemical Society,1978,vol. 55,p. 1054 - 1055.

3
[ 828-81-9 ]
[ 79-04-9 ]
[ 18199-97-8 ]

Yield	Reaction Conditions	Operation in experiment
61%	With TEA; In dichloromethane; for 2h;Reflux;	General procedure: Compounds 6{10 (5 mmol) were dissolved in DCM and TEA (6 mmol) was added to the reactionmixtures. alpha-Chloroacetyl chloride (10 mmol) was slowly added to the reaction mixtures. The reaction mixtureswere heated for 2 h under reux. The reaction was checked with TLC. The crude products were ltered, dried,and crystallized from 1,4-dioxane to obtain products 11-15.

References: [1]Archiv der Pharmazie,2015,vol. 348,p. 10 - 22.
[2]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 2345 - 2350.
[3]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 1011 - 1016.
[4]Synthetic Communications,2008,vol. 38,p. 973 - 982.
[5]Turkish Journal of Chemistry,2018,vol. 42,p. 839 - 858.
[6]Pharmazie,1967,vol. 22,p. 434 - 436.

4
[ 828-81-9 ]
[ 75-05-8 ]
[ 70080-97-6 ]

References: [1]Journal of the Indian Chemical Society,1978,vol. 55,p. 1054 - 1055.

5
[ 828-81-9 ]
[ 121-60-8 ]
[ 980-28-9 ]

References: [1]Journal of the Indian Chemical Society,1964,vol. 41,p. 295 - 298.

6
[ 5706-78-5 ]
[ 828-81-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With iron(III) chloride; In ethanol;Reflux;	General procedure: Compounds 1{5 (1 mmol) were dissolved in ethanol and ethanolic ferric chloride solution (4 mmol) wasadded. The reaction mixtures were heated under reux for 16{20 h. The mixtures were neutralized usingammonia solution, ltered and washed with water, dried, and crystallized from ethanol to obtain compounds 6-10.
	With iodosylbenzene; dihydrogen peroxide; acetic acid; In dimethyl sulfoxide; at 60℃; for 4h;Green chemistry;	General procedure: To a mixture of thiosemicarbazide (3, 0.5mmol), sodiumacetate (0.5mmol), aldehyde (2, 0.5mmol), 3mL of solvent(vH2O:vEtOH=1:1) was successively added into the tube andstirred for 15min at room temperature. After the reactionwas completed, the solvent was evaporated under reducedpressure and the residue was redissolved in DMSO (3mL),followed by addition of acetic acid (2 equiv), PhI (10mol%)and H2O2(2 equiv) in sequence, and then stirred at 60Cfor 4h (monitored by TLC). After allowing to attain roomtemperature, the saturated solution of Na2S2O3(5mL) wasadded to the reaction mixture in order to quench and then themixture was extracted with ethyl acetate (3 × 10mL). Thecombined organic layer was dried over anhydrous MgSO4and concentrated. Finally, the residue was purified by flashcolumn chromatography on silica gel using a mixture of ethylacetate and petroleum ether as eluent to give the products.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5735 - 5738.
[2]ACS Infectious Diseases,2019.
[3]Turkish Journal of Chemistry,2018,vol. 42,p. 839 - 858.
[4]Archiv der Pharmazie,2015,vol. 348,p. 10 - 22.
[5]Indian Journal of Chemistry,1970,vol. 8,p. 509 - 513.
[6]Journal of Enzyme Inhibition and Medicinal Chemistry,2014,vol. 29,p. 611 - 618.
[7]Medicinal Chemistry Research,2016,vol. 25,p. 1193 - 1203.
[8]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1872 - 1879.
[9]Catalysis Letters,2018,vol. 148,p. 3486 - 3491.

7
[ 830-86-4 ]
[ 828-81-9 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 103 - 105.
[2]Journal of the Indian Chemical Society,1964,vol. 41,p. 295 - 298.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 518 - 520.
[4]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 1023 - 1027.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 475 - 481.
[6]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4919 - 4923.

8
[ 50-00-0 ]
[ 90-33-5 ]
[ 828-81-9 ]
8-[5-(2-Chloro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-methyl}-7-hydroxy-4-methyl-chromen-2-one [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 984 - 985.

9
[ 50-00-0 ]
[ 828-81-9 ]
[ 2747-05-9 ]
Acetic acid 8-[5-(2-chloro-phenyl)-[1,3,4]thiadiazol-2-ylamino]-methyl}-4-methyl-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 984 - 985.

10
[ 828-81-9 ]
[ 5067-90-3 ]
[ 79225-82-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 518 - 520.

11
[ 828-81-9 ]
[ 104-88-1 ]
[ 122772-38-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 998 - 1001.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 78 - 80.
[3]Journal of the Indian Chemical Society,1994,vol. 71,p. 201 - 202.

12
[ 828-81-9 ]
[ 58903-20-1 ]
[ 79225-87-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 518 - 520.

13
[ 828-81-9 ]
[ 100-52-7 ]
[ 84304-48-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 480 - 481.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 998 - 1001.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 2583 - 2588.

14
[ 828-81-9 ]
[ 75-87-6 ]
[ 344349-04-8 ]

References: [1]Agricultural and Biological Chemistry,1983,vol. 47,p. 103 - 105.

15
[ 828-81-9 ]
[ 532-55-8 ]
[ 79225-76-6 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1981,vol. 20,p. 518 - 520.

16
[ 828-81-9 ]
[ 36894-93-6 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 902 - 906.

17
[ 79-19-6 ]
[ 118-91-2 ]
[ 828-81-9 ]

Yield	Reaction Conditions	Operation in experiment
88%		General procedure: 5.1.1 5-(4-Morpholinophenyl)-1,3,4-thiadiazol-2-amine (59) A mixture of 4-morpholinobenzoic acid (5.18 g, 25 mmol) and N-aminothiourea (2.28 g, 25 mmol) in POCl3 (7 ml) was stirred vigorously at 75 C for 0.5 h. After addition of H2O (30 ml), the reaction mixture was heated under reflux for 4 h and basified to pH 8 by 50% NaOH solution. The mixture was filtered and the filter cake was recrystallized from ethanol to yield 3.90 g of compound 59 as a yellow crystal. Yield: 59%; The synthetic procedures of compounds 60-81 were the same as that described above. 5.1.1.9 5-(2-Chlorophenyl)-1,3,4-thiadiazol-2-amine (68) Yield: 88%, mp: 190-192 C (EtOH). ESI-MS m/z: 212.1 [M+H]+; 1H NMR (CDCl3) delta 7.45-7.50 (m, 4H), 7.60-7.62 (m, 1H), 7.99-8.01 (m, 1H).
86%	With trichlorophosphate; In water; at 100 - 120℃; for 2h;	General procedure: A mixture of benzoic acid (5.0 g, 40.94 mmol), thiosemicarbazide(3.67 g, 40.26 mmol) and phosphorus oxychloride(9.25 mL) was refluxed under continuous stirring. Thereaction mixture was cooled to room temperature and wasrefluxed further for 2 h after the addition of water (55 mL).After cooling, the mixture was basified to pH 9 by dropwise addition of 50% sodium hydroxide solution. The solidso obtained was filtered, dried and recrystallised fromethanol to afford 4a (5.65 g, 78%), m.p. 221-223 C (Lit.224-225 C) (Guan et al. 2014). The same procedure was performed with 2-chloro benzoicacid with a reflux of 6 h to yield 4b (5.81 g, 86%), m.p.220-222 C (Lit. 220-221 C).
80%	With trichlorophosphate; at 20℃; for 4.5h;Reflux;	General procedure: 4.2.2.1. 5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-amine (2b). A mixture of 4-fluoro benzoic acid (5.0 g, 35.70 mmol), thiosemicarbazide (3.25 g, 35.70 mmol) and POCl3 (9.25 ml)was heated to 75 C and maintained same temperature for 30 min under stirring. The reaction mixture cooled to room temperature, water (55 ml) was added and refluxed for 4 h. After cooling, the mixture was basified with 50% NaOH to pH 8 by the drop wise addition under stirring. The obtained solid was filtered and recrystallized from ethanol to give the target compound 2b as a colorless solid. Yield: 5.69 g, 82%

		General procedure: The each substituted benzoic acid (6.001 g, 0.05 mol), thiosemicarbazide (4.557 g, 0.05 mol) and POCl3 (13 ml) were thoroughly stirred, mixed and heated at 75 C for 1 h with constant stirring. After cooling to rt, water (40ml) was slowly added. The reaction mixture was further refluxed for 4h. After cooling, the mixture was basified to pH 8 by careful drop wise addition of 10% aqueous ammonia solution with constant stirring. The precipitate thus obtained was filtered and recrystallized from ethanol: water mixture to yield the pure compounds (2a-e) [13].
		General procedure: Substituted-5-phenyl-1, 3, 4-thiadiazol-2-amine (5)was synthesized by according to reportedliterature 2 Equimolar mixture of substituted benzoicacid and semicarbazide in 100ml round bottom flask,POCl3(13 ml) were added to it and heated at 75 0Cfor half an hour. After cooling down to roomtemperature then add water. The reaction mixturewas reflux for 4 hr, after cooling the mixture wasbasified to PH-8 by drop wise addition of 50 %NaOH solution under the stirring. The precipitatewas filtered and recrystallized from ethanol toobtained pure yield of compounds. 5-phenyl-1,3,4-thiadiazol-2-amine
		General procedure: A mixture ofcorresponding acid, 1 (2.00 mmol), and POCl3 (0.80 ml) wasstirred for 20 min at room temperature. Then, thiosemicarbazide(2.0 mmol, 0.182 g) was added, and theresulting suspension was refluxed for 1 h. After cooling theflask in an ice bath, 2.4 ml of distilled water was addedcarefully, and refluxwas continued for 1 h. The mixturewasthen cooled to the room temperature, saturated aqueoussolution of NaOH was added until pH 8.5 was reached, andthe suspensionwas stirred for 1 h at the room temperature.The formed precipitate of the corresponding 2-amino-1,3,4-thiadiazole derivative (2aeo) was then filtrated, driedover CaCl2, and recrystallized from hot 50% aqueous EtOH.
	With trichlorophosphate; at 20 - 70℃; for 2.5h;	General procedure: 10 mL of phosphorus oxychloride was added to the raw materials of acetic acid (10mmol) and hydrazinecarbothioamine in a 50 mL flask. The mixture was stirred at room temperature for 0.5 h, and then heated up to 70C for 2 h. After cooling to room temperature, 40 mL of distilled water was added slowly to quench the phosphorus oxychloride. Then, the mixture was heated and refluxed for 5 h. When the solution was neutralized by adding 50% NaOH solution to pH=8, the product was precipitated. The raw product was purified by MeOH or flash column chromatography. Yield: 75%.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 998 - 1001.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5766 - 5775.
[3]Medicinal Chemistry Research,2018,vol. 27,p. 1800 - 1821.
[4]Medicinal Chemistry Research,2012,vol. 21,p. 816 - 824.
[5]Journal of Chemical Research,2014,vol. 38,p. 347 - 350.
[6]European Journal of Medicinal Chemistry,2015,vol. 95,p. 49 - 63.
[7]Journal of Chemical Research,2011,vol. 35,p. 703 - 706.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2003,vol. 42,p. 2583 - 2588.
[9]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 2345 - 2350.
[10]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 1011 - 1016.
[11]Journal of Medicinal Chemistry,2013,vol. 56,p. 6761 - 6774.
[12]Journal of Medicinal Chemistry,1988,vol. 31,p. 902 - 906.
[13]Heterocyclic Communications,2007,vol. 13,p. 387 - 392.
[14]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2782 - 2786.
[15]Indian Journal of Heterocyclic Chemistry,2011,vol. 20,p. 403 - 404.
[16]European Journal of Medicinal Chemistry,2015,vol. 95,p. 514 - 525.
[17]Medicinal Chemistry Research,2015,vol. 24,p. 4058 - 4069.
[18]Oriental Journal of Chemistry,2015,vol. 31,p. 1873 - 1885.
[19]Bioorganic Chemistry,2018,vol. 81,p. 88 - 92.
[20]Indian Journal of Heterocyclic Chemistry,2014,vol. 23,p. 311 - 314.
[21]Comptes Rendus Chimie,2019,vol. 22,p. 585 - 598.
[22]Chemical Biology and Drug Design,2020,vol. 95,p. 174 - 181.
[23]Bioorganic and medicinal chemistry letters,2020.

18
[ 828-81-9 ]
[ 99-91-2 ]
2-(o-chlorophenyl)-6-(p-chlorophenyl)-imidazo<2,1-b>-1,3,4-thiadiazole [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 686 - 687.

19
[ 828-81-9 ]
[ 536-38-9 ]
2-(o-chlorophenyl)-6-(p-chlorophenyl)-imidazo<2,1-b>-1,3,4-thiadiazole [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 686 - 687.

20
[ 828-81-9 ]
[ 158979-77-2 ]
[ 158980-03-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 350 - 354.

21
[ 828-81-9 ]
[ 158979-74-9 ]
[ 158980-00-8 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 350 - 354.

22
[ 828-81-9 ]
[ 2747-08-2 ]
C₁₉H₁₄ClN₃O₂S [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1993,vol. 70,p. 649 - 650.

23
[ 828-81-9 ]
2-Bromo-6-ethoxy-5-methoxy-indan-1-one [ No CAS ]
C₂₀H₁₆ClN₃O₂S [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1993,vol. 70,p. 649 - 650.

24
[ 828-81-9 ]
[ 166116-63-8 ]
4-[[5-(2-Chloro-phenyl)-3H-[1,3,4]thiadiazol-(2Z)-ylideneamino]-(4-fluoro-phenyl)-methyl]-2-methyl-4H-oxazol-5-one [ No CAS ]
(S)-4-[(R)-[5-(2-Chloro-phenyl)-3H-[1,3,4]thiadiazol-(2E)-ylideneamino]-(4-fluoro-phenyl)-methyl]-2-methyl-4H-oxazol-5-one [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 500 - 503.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 500 - 503.

25
[ 828-81-9 ]
[ 166116-63-8 ]
N-[(6R,7S)-2-(2-Chloro-phenyl)-7-(4-fluoro-phenyl)-5-oxo-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-6-yl]-acetamide [ No CAS ]
N-[(6R,7R)-2-(2-Chloro-phenyl)-7-(4-fluoro-phenyl)-5-oxo-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-6-yl]-acetamide [ No CAS ]

26
[ 828-81-9 ]
[ 166116-62-7 ]
4-[[5-(2-Chloro-phenyl)-3H-[1,3,4]thiadiazol-(2Z)-ylideneamino]-(4-fluoro-phenyl)-methyl]-2-phenyl-4H-oxazol-5-one [ No CAS ]
(S)-4-[(R)-[5-(2-Chloro-phenyl)-3H-[1,3,4]thiadiazol-(2E)-ylideneamino]-(4-fluoro-phenyl)-methyl]-2-phenyl-4H-oxazol-5-one [ No CAS ]

27
[ 828-81-9 ]
[ 166116-62-7 ]
N-[(6R,7S)-2-(2-Chloro-phenyl)-7-(4-fluoro-phenyl)-5-oxo-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-6-yl]-benzamide [ No CAS ]
N-[(6R,7R)-2-(2-Chloro-phenyl)-7-(4-fluoro-phenyl)-5-oxo-6,7-dihydro-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-6-yl]-benzamide [ No CAS ]

28
[ 828-81-9 ]
[ 333-20-0 ]
[ 170950-31-9 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 828 - 831.

29
[ 828-81-9 ]
[ 259794-91-7 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 998 - 1001.
[2]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 1023 - 1027.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 475 - 481.
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4919 - 4923.

31
[ 828-81-9 ]
[ 2740-81-0 ]
1-(2-chloro-phenyl)-3-[5-(2-chloro-phenyl)-[1,3,4]thiadiazol-2-yl]-thiourea [ No CAS ]