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Chemical Structure| 3704-41-4 Chemical Structure| 3704-41-4

Structure of 3704-41-4

Chemical Structure| 3704-41-4

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Product Details of [ 3704-41-4 ]

CAS No. :3704-41-4
Formula : C9H6N2O2S
M.W : 206.22
SMILES Code : O=[N+](C1=CC=C(C2=NC=CS2)C=C1)[O-]
MDL No. :MFCD26794836
InChI Key :LGDOGDJADXLHLA-UHFFFAOYSA-N
Pubchem ID :13546655

Safety of [ 3704-41-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 3704-41-4 ]

* 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 [ 3704-41-4 ]

[ 3704-41-4 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1826-11-5 ]
  • [ 3704-41-4 ]
YieldReaction ConditionsOperation in experiment
58.6% With sulfuric acid; nitric acid; In water; at 0℃; for 1h; A solution of 2-phenyl thiazole (200mg, 1.24mmol) in cone, sulphuric acid (0.5ml) was cooled to O0C. The nitrating mixture (made up of 0.5ml of cone, nitric acid and 0.5ml of cone, sulfuric acid) was added dropwise and stirred at O0C for lhr. The reaction was quenched with ice water and basified with sodium hydroxide solution. The resultant precipitate was filtered and washed with water. Purification by column chromatography over silica gel using EtOAc/ pet ether gave 2-(4-nitrophenyl) thiazole (150mg, 58.6%) as solid.
  • 2
  • [ 3704-41-4 ]
  • [ 193017-26-4 ]
YieldReaction ConditionsOperation in experiment
88% With iron; In acetic acid; at 20℃; for 2h; Iron powder (0.5g, 8.92mmol) was added portion wise to a solution of 2-(4- nitrophenyl)-thiazole (200mg, 0.97mmol) in acetic acid (5ml) and stirred at room temperature for 2hr. The reaction mixture was diluted with water, basified with dilute sodium hydroxide, filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water, brine and dried. Evaporation of the solvent yielded 4- thiazol-2-yl-phenylamiiie (150mg, 88%) as solid.
  • 3
  • [ 3704-41-4 ]
  • [ 193017-26-4 ]
  • bis-(4-thiazol-2-yl-phenyl)-diazene-<i>N</i>-oxide [ No CAS ]
  • 5
  • [ 288-47-1 ]
  • [ 636-98-6 ]
  • [ 3704-41-4 ]
YieldReaction ConditionsOperation in experiment
With N,N'-disalicylideneethylenediamine; caesium carbonate;copper(l) iodide; cobalt(II) acetate; In 1,4-dioxane; at 150℃; for 10h; Preparation of 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-thia-3,3b,5-triaza-cyclopenta[a]pentalen-5-yl]-butyric acid ethyl ester (Compound 37) As depicted in Scheme 24 below, anhydrous Co(OAc)2 (0.021 mmol, 5%) and SALEN (2,2'-(1,4-diiminobutane-1,4-diyl)diphenol, 0.041 mmol, 0.1 molequivalent) in 0.5 ml dry dioxane are placed in a flame-dried flask, and the mixture is stirred for 10 minutes at room temperature. A solution of thiazole (0.411 mmol) in 1 ml dry dioxane, anhydrous Cs2CO3 (0.493 mmol, 1.2 molequivalents) and CuI (0.822 mmol, 2 molequivalents) are thereafter added consecutively to the reaction mixture under argon. A solution of 4-nitrophenyl iodide (0.493 mmol, 1.2 molequivalents) in dry dioxane (0.5 ml) is then added dropwise and the resulting mixture is heated to 150 C. under argon, while monitoring the reaction progress by TLC. Once the reaction is completed (after about 10 hours), the resulting mixture is diluted with chloroform (20 ml) and filtered through a celite pad. The organic solvents are evaporated under reduced pressure and the crude product is purified by flash column chromatography, using a hexane:ethyl acetate mixture as eluent, to give pure 2-[4-nitrophenyl]thiazole.
  • 6
  • [ 3704-41-4 ]
  • [ 25020-24-0 ]
  • 7
  • [ 3704-41-4 ]
  • [ 25020-25-1 ]
  • 8
  • [ 3704-41-4 ]
  • [ 25020-38-6 ]
  • 9
  • [ 3704-41-4 ]
  • [ 25020-27-3 ]
  • 10
  • [ 3704-41-4 ]
  • [ 25020-26-2 ]
  • 11
  • [ 3704-41-4 ]
  • [ 25020-36-4 ]
  • 12
  • [ 3704-41-4 ]
  • [ 25020-28-4 ]
  • 13
  • [ 3704-41-4 ]
  • [ 25020-37-5 ]
  • 14
  • [ 4394-85-8 ]
  • [ 3704-41-4 ]
  • [ 185245-02-7 ]
YieldReaction ConditionsOperation in experiment
As depicted in Scheme 25 below, <strong>[3704-41-4]2-(4-nitrophenyl)thiazole</strong> (19.9 mmol) dissolved in ether (20 ml) is added dropwise over 1 hour to a stirred and cooled (-78 C.) solution of butyl lithium (1.5 M) in n-hexane (20 ml, 29.9 mmol), diluted with ether (50 ml). The mixture is stirred at -78 C. for 30 minutes and then a solution of N-formylmorpholine (29.9 mmol) in ether (30 ml) is added dropwise over a time period of 15 minutes. After 30 minutes at -78 C., the mixture is washed with saturated aqueous NaHCO3 (30 ml) and extracted with ether (2*20 ml). The organic phase is dried over Na2SO4 and the solvent is removed under reduced pressure to give the crude <strong>[3704-41-4]2-(4-Nitro-phenyl)-thiazol</strong>e-5-carbaldehyde.
  • 15
  • [ 2518-13-0 ]
  • [ 3704-41-4 ]
  • 16
  • [ 619-72-7 ]
  • [ 3704-41-4 ]
  • 17
  • [ 288-47-1 ]
  • [ 3466-32-8 ]
  • [ 3704-41-4 ]
  • 18
  • [ 3704-41-4 ]
  • [ 141-32-2 ]
  • (E)-butyl 3-(2-(4-nitrophenyl)thiazol-5-yl)acrylate [ No CAS ]
  • 19
  • [ 2227-79-4 ]
  • [ 3704-41-4 ]
  • 20
  • [ 288-47-1 ]
  • [ 456-27-9 ]
  • [ 3704-41-4 ]
  • 21
  • [ 3704-41-4 ]
  • 2-(4-nitrophenyl)-4H-pyrrolo[2,3-d]-thiazole-5-carboxylic acid ethyl ester [ No CAS ]
  • 22
  • [ 3704-41-4 ]
  • 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-thia-3,3b,5-triaza-cyclopenta[a]pentalen-5-yl]-butyric acid ethyl ester [ No CAS ]
  • 23
  • [ 3704-41-4 ]
  • C14H11N5O4S [ No CAS ]
  • 24
  • [ 3034-53-5 ]
  • [ 24067-17-2 ]
  • [ 3704-41-4 ]
YieldReaction ConditionsOperation in experiment
56.00% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; toluene; at 80℃; for 12h;Inert atmosphere; A mixture of 4-nitrophenyl)boronic acid (23.00 g, 137.78 mmol, 1.00 eq.), 2-bromothiazole (25.54 g, 155.69 mmol, 14.03 mL, 1.13 eq.), Na2C03 (36.51 g, 344.45 mmol, 2.50 eq.) and Pd(dppf)Cl2.CH2Cl2 (6.75 g, 8.27 mmol, 0.06 eq.) in Tol. (250.00 mL)/H20 (100.00 mL)/dioxane (250.00 mL) was degassed and purged with N2 for 3 times. The mixture was stirred at 80C for 12 hrs under N2 atmosphere and LCMS showed the reaction was complete. The mixture was concentrated and the residue was purified by column chromatography (Petroleum ethenEthyl acetate=50: l to 5: 1) to give 2-(4-nitrophenyl)thiazole (14.00 g, 67.89 mmol, 56.00% yield) as a yellow solid. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.35 - 8.29 (m, 2H), 8.21 - 8.12 (m, 2H), 7.99 (d, J = 3.2 Hz, 1H), 7.50 (d, J = 3.2 Hz, 1H).
  • 25
  • [ 3704-41-4 ]
  • N-[3-(tert-butylsulfamoyl)-4-[2-(4-nitrophenyl)thiazol-5-yl]phenyl]acetamide [ No CAS ]
  • 26
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[4-acetamido-2-(tert-butylsulfamoyl)phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 27
  • [ 3704-41-4 ]
  • N-[4-[2-(4-aminophenyl)thiazol-5-yl]-3-(tert-butylsulfamoyl)phenyl]acetamide [ No CAS ]
  • 28
  • [ 3704-41-4 ]
  • tert-butyl N-[4-[5-[4-acetamido-2-(tert-butylsulfamoyl)phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 29
  • [ 3704-41-4 ]
  • tert-butyl (2S)-2-[[3-(tert-butylsulfamoyl)-4-[2-[4-(isopropoxycarbonylamino)phenyl]thiazol-5-yl]phenyl]carbamoyl]pyrrolidine-1-carboxylate [ No CAS ]
  • 30
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[2-(tert-butylsulfamoyl)-4-(ethylamino)phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 31
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[2-(tert-butylsulfamoyl)-4-hydroxyphenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 32
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[2-(tert-butylsulfamoyl)-4-(2,2,2-trifluoroethylamino)phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 33
  • [ 3704-41-4 ]
  • C27H34N4O5S2 [ No CAS ]
  • 34
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[4-amino-2-(tert-butylsulfamoyl)phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
  • 35
  • [ 3704-41-4 ]
  • isopropyl N-[4-[5-[2-(tert-butylsulfamoyl)-4-[(2,2,2-trifluoro-1-methylethyl)amino]phenyl]thiazol-2-yl]phenyl]carbamate [ No CAS ]
 

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Technical Information

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