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Chemical Structure| 20143-41-3
Chemical Structure| 20143-41-3
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CAS No. :20143-41-3 MDL No. :MFCD02295746
Formula : C8H6Cl2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 205.04 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 20143-41-3 ]

* 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 [ 20143-41-3 ]

[ 20143-41-3 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 614-61-9 ]
  • [ 20143-41-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;Reflux; General procedure: The 2-amino-5-mercapto-1,3,4-thiadiazole 1 (5 mmol) was dissolved in NaOH(5 mmol, 15 mL) at room temperature. Ethyl 2-bromopropionate (5 mmol) was addedto the solution obtained and the mixture was stirred for 20 min. After that, the solid precipitatewas filtered off, washed with cold water, air dried, and then recrystallized from ethanolto give 2-(5-amino-1,3,4-thiadiazol-2-ylthio) propanoate 2 in 78% yield as pale yellowsolid. Mp 79-80C; 1H NMR(CDCl3, 400 MHz) δH: 1.25-1.28 (t, 3H, CH3, J = 6.0 Hz),1.57-1.59 (d, 3H, CH3, J = 8.0 Hz), 4.03-4.08 (q, 1H, SCH, J = 12.0 Hz), 4.16-4.22(q, 2H, OCH2, J = 16.0 Hz).4.35 (s, 2H, NH2); 13C NMR (CDCl3, 400 MHz) δC: 14.0,17.5, 46.0, 61.8, 150.0, 170.9, 171.4; IR (KBr) ν: 3266 (NH2), 1736 (OC O), 1501,1449, 1321, 1094 (C N N C S) cm-1; Anal. calcd for C7H11N3O2S2: C36.04, H 4.75,N 18.01; found C 36.10, H 4.77, N 17.93.To a 50 mL round-bottom flask was added phenoxyalkanoic acid 4 (5 mmol) andSOCl2 (5 mL). The mixture was refluxed for 4 h, and the excess SOCl2 was removedunder vacuum. The crude diacyl chloride was dissolved in CH3CN (5 mL) and addeddropwise through a dropping funnel to themixture of 2-(5-amino-1,3,4-thiadiazol-2-ylthio)propanoate 2 (4.5 mmol) and Et3N (4.2 mL, 30 mmol) in CH3CN (15 mL) on an ice bath.This mixture was vigorously stirred at room temperature for an additional 12 h aftercompletion of the addition. The product was evaporated under reduced pressure washedwith water and brine, dried and recrystallized from ethanol to give the title compounds 6.
With phosphorus pentachloride; In dichloromethane;Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
With thionyl chloride; In toluene;Reflux; Acid 2 (2.20mmol; 0.42g) was dissolved in 12mL toluene and SOCl2 (82.3mmol; 6.00mL) was added. The mixture was refluxed overnight, and the solvent was removed on high vacuum to give the crude acyl chloride. This product was dissolved in a small amount of THF and added to a solution of methyl 2-amino-4-cyanobenzoate (2.00mmol; 0.35g) and K2CO3 (4.00mmol; 0.55g) in THF (29ml) stirred for 15minat RT. The reaction mixture was stirred at RT for 4h until the reaction was complete. The reaction was diluted with water (30mL) and extracted with EtOAc (3×30mL). The combined organics were washed with brine, dried with Na2SO4 and evaporated to dryness. The crude product was recrystallized in acetonitrile to give white crystals (0.55g; 80%). 1H NMR (400MHz, CDCl3) δ 11.90 (s, 1H), 9.16 (d, J=1.4Hz, 1H), 8.13 (d, J=8.2Hz, 1H), 7.42 (ddd, J=12.3, 8.0, 1.5Hz, 2H), 7.25 (td, J=8.0, 1.6Hz, 1H), 7.05-6.96 (m, 2H), 4.72 (s, 2H), 3.95 (s, 3H). 13C NMR (101MHz, CDCl3) δ 167.45, 166.71, 153.10, 140.55, 131.72, 130.96, 128.10, 126.38, 124.51, 123.86, 123.53, 119.61, 117.77 (d, J=5.3Hz), 114.82, 69.11, 53.13. HRMS m/z [M+ H]+ calcd for C17H14ClN2O4 345.0637, found: 345.0627. mp: 159.6-160.1C.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 3h; General procedure: To a solution of the acid (22a-g) (1.2 eq.) in DCM, oxalyl chlorideand 1 drop DMF were added dropwise at 0 C. After 3 h, DCM wasremoved by rotary evaporation. The resulting acyl chloride dissolvedin THF and pyridine was added dropwise into a solution of26 (1.0 eq.) in THF at 0 C, then slowly warmed to r.t. and continuedstirring for 5e6 h. 1 M HCl was added and extracted with ethylacetate for three times. The organic layer was combined, washedwith brine for once, dried over anhydrous Na2SO4 and concentratedto afford compounds 27a-g. To the solution of 27a-g in ethyl acetate,HCl gaswas added for 0.5 h, and the resulting solidwas filteredto obtain desired compounds 28a-g.

Reference: [1]Journal of the Chemical Society,1922,vol. 121,p. 1603
[2]Journal of Medicinal Chemistry,1972,vol. 15,p. 940 - 944
[3]Chemical and Pharmaceutical Bulletin,1988,vol. 36,p. 4426 - 4434
[4]Archiv der Pharmazie,1983,vol. 316,p. 431 - 434
[5]Journal of the Indian Chemical Society,1991,vol. 68,p. 163 - 165
[6]Journal of the Indian Chemical Society,1992,vol. 69,p. 45 - 46
[7]Journal of the Indian Chemical Society,1992,vol. 69,p. 402 - 403
[8]Journal of the Indian Chemical Society,1996,vol. 73,p. 627 - 628
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 514 - 516
[10]Russian Journal of Organic Chemistry,2000,vol. 36,p. 240 - 244
[11]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4726 - 4733
[12]Asian Journal of Chemistry,2012,vol. 24,p. 1223 - 1226
[13]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 7581 - 7587
[14]Phosphorus, Sulfur and Silicon and the Related Elements,2013,vol. 188,p. 989 - 994
[15]Journal of Medicinal Chemistry,2014,vol. 57,p. 2380 - 2392
[16]Phosphorus, Sulfur and Silicon and the Related Elements,2014,vol. 189,p. 1337 - 1345
[17]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 183 - 187
[18]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 165 - 170
[19]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 6267 - 6272
[20]British Journal of Pharmacology,2018,vol. 175,p. 2504 - 2519
[21]European Journal of Medicinal Chemistry,2019,vol. 166,p. 167 - 177
[22]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 10489 - 10497
[23]European Journal of Medicinal Chemistry,2020,vol. 185
[24]Russian Journal of Organic Chemistry,2020,vol. 56,p. 802 - 812
    Zh. Org. Khim.,2020,vol. 56,p. 753 - 765,13
  • 2
  • [ 6313-37-7 ]
  • [ 20143-41-3 ]
  • (2-chloro-phenoxy)-acetic acid-(2,5-dimethoxy-4-nitro-anilide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine
  • 3
  • [ 30709-67-2 ]
  • [ 20143-41-3 ]
  • [ 72192-49-5 ]
  • 4
  • [ 75057-62-4 ]
  • [ 20143-41-3 ]
  • [ 75057-59-9 ]
  • 5
  • [ 20143-41-3 ]
  • [ 20776-54-9 ]
  • [ 75057-60-2 ]
  • 6
  • [ 20143-41-3 ]
  • [ 16942-66-8 ]
  • [ 72192-55-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene
  • 7
  • [ 364-62-5 ]
  • [ 20143-41-3 ]
  • [ 65569-40-6 ]
YieldReaction ConditionsOperation in experiment
72.4% With triethylamine In toluene for 6h; Heating;
  • 8
  • [ 67-56-1 ]
  • [ 20143-41-3 ]
  • [ 6956-85-0 ]
  • 9
  • [ 20143-41-3 ]
  • [ 344-72-9 ]
  • N-(4-trifluoromethyl-5-ethoxycarbonyl-thiazol-2-yl)-2-(2-chlorophenoxy)acetamide [ No CAS ]
  • 10
  • [ 17647-70-0 ]
  • [ 20143-41-3 ]
  • 2-(2-chlorophenoxy)-N-(4-methyl-1,2,3-oxadiazol-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
177 mg In dichloromethane Reflux; General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
  • 11
  • [ 20143-41-3 ]
  • [ 5372-81-6 ]
  • dimethyl 2-(2-(2-chlorophenoxy)acetamido)terephthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: dimethyl aminoterephthalate With potassium carbonate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: (2-chloro-phenoxy)-acetyl chloride In tetrahydrofuran at 20℃; for 2.5h;
  • 12
  • [ 46004-37-9 ]
  • [ 20143-41-3 ]
  • methyl 2-chloro-4-(2-(2-chlorophenoxy)acetamido)benzoate [ No CAS ]
  • 13
  • [ 20143-41-3 ]
  • [ 159847-83-3 ]
  • methyl 2-(2-(2-chlorophenoxy)acetamido)-4-cyanobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium carbonate; In tetrahydrofuran; at 20℃; for 4.25h; Acid 2 (2.20mmol; 0.42g) was dissolved in 12mL toluene and SOCl2 (82.3mmol; 6.00mL) was added. The mixture was refluxed overnight, and the solvent was removed on high vacuum to give the crude acyl chloride. This product was dissolved in a small amount of THF and added to a solution of <strong>[159847-83-3]methyl 2-amino-4-cyanobenzoate</strong> (2.00mmol; 0.35g) and K2CO3 (4.00mmol; 0.55g) in THF (29ml) stirred for 15minat RT. The reaction mixture was stirred at RT for 4h until the reaction was complete. The reaction was diluted with water (30mL) and extracted with EtOAc (3×30mL). The combined organics were washed with brine, dried with Na2SO4 and evaporated to dryness. The crude product was recrystallized in acetonitrile to give white crystals (0.55g; 80%). 1H NMR (400MHz, CDCl3) delta 11.90 (s, 1H), 9.16 (d, J=1.4Hz, 1H), 8.13 (d, J=8.2Hz, 1H), 7.42 (ddd, J=12.3, 8.0, 1.5Hz, 2H), 7.25 (td, J=8.0, 1.6Hz, 1H), 7.05-6.96 (m, 2H), 4.72 (s, 2H), 3.95 (s, 3H). 13C NMR (101MHz, CDCl3) delta 167.45, 166.71, 153.10, 140.55, 131.72, 130.96, 128.10, 126.38, 124.51, 123.86, 123.53, 119.61, 117.77 (d, J=5.3Hz), 114.82, 69.11, 53.13. HRMS m/z [M+ H]+ calcd for C17H14ClN2O4 345.0637, found: 345.0627. mp: 159.6-160.1C.
  • 14
  • [ 20143-41-3 ]
  • [ 18595-13-6 ]
  • methyl 2-(2-(2-chlorophenoxy)acetamido)-6-methylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; In tetrahydrofuran; at 20℃; for 4.25h; Acid 2 (1.10mmol; 0.20g) was dissolved in 12mL toluene and SOCl2 (82.3mmol; 6.00mL) was added. The mixture was refluxed overnight, and the solvent was removed on high vacuum to give the crude acyl chloride. This product was dissolved in a small amount of THF and added to a solution of <strong>[18595-13-6]methyl 2-amino-6-methyl-benzoate</strong> (1.00mmol; 0.17g) and K2CO3 (2.00mmol; 0.28g) in THF (17ml) stirred for 15minat RT. The reaction mixture was stirred at RT for 3h until the reaction was complete. The reaction was diluted with water (30mL) and extracted with EtOAc (3×30mL). The combined organics were washed with brine, dried with Na2SO4 and evaporated to dryness to give a brown oil which was used without further purification (0.39g; 99%). 1H NMR (300MHz, CDCl3) delta 10.07 (s, 1H), 8.17 (d, J= 8.3Hz, 1H), 7.44 (dd, J= 7.9, 1.6Hz, 1H), 7.37 (t, J= 8.0Hz, 1H), 7.24 (dd, J= 8.1, 1.6Hz, 1H), 7.06-7.00 (m, 2H), 7.00-6.92 (m, 1H), 4.68 (s, 2H), 3.85 (s, 3H), 2.43 (s, 3H). 13C NMR (75MHz, CDCl3) delta 168.47, 166.39, 153.12, 138.68, 136.37, 131.50, 130.82, 128.15, 127.49, 123.59, 123.27, 122.25, 120.25, 114.45, 68.93, 52.32, 21.88. HRMS m/z [M+ H]+ calcd for C17H17ClNO4 334.0841, found: 334.0845.
  • 15
  • [ 135484-83-2 ]
  • [ 20143-41-3 ]
  • methyl 4-bromo-2-(2-(2-chlorophenoxy)acetamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
3% With potassium carbonate; In tetrahydrofuran; at 20℃; for 4.25h; Acid 2 (21.4mmol; 4.00g) was dissolved in 16mL toluene and SOCl2 (107mmol; 7.82mL) was added. The mixture was refluxed overnight, and the solvent was removed on high vacuum to give the crude acyl chloride. This product was dissolved in a small amount of THF and added to a solution of <strong>[135484-83-2]methyl 2-amino-4-bromobenzoate</strong> (19.4mmol; 4.48g) and K2CO3 (38.9mmol; 5.38g) in THF (115ml) stirred for 15minat RT. The reaction mixture was stirred at RT overnight until the reaction was complete. The reaction was diluted with water (30mL) and extracted with EtOAc (3×30mL). The combined organics were washed with brine, dried with Na2SO4 and evaporated to dryness to give the pure product as a brown solid (6.40g; 83%). 1H NMR (400MHz, CDCl3) delta 11.88 (s, 1H), 9.02 (d, J=1.9Hz, 1H), 7.89 (d, J=8.5Hz, 1H), 7.44 (dd, J=7.7, 1.5Hz, 1H), 7.29 (dd, J=8.5, 2.0Hz, 1H), 7.23 (dd, J=7.8, 1.5Hz, 1H), 7.06-6.96 (m, 2H), 4.71 (s, 2H), 3.90 (s, 3H). 13C NMR (101MHz, CDCl3) delta 167.51, 167.21, 153.28, 141.04, 132.13, 130.94, 129.40, 128.06, 126.76, 123.96, 123.91, 123.41, 115.12, 114.84, 69.26, 52.67. HRMS m/z [M+ Na]+ calcd for C16H13BrClNO4Na 419.9609, found: 419.9601. mp: 127.1-130.2C.
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