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Chemical Structure| 2866-43-5 Chemical Structure| 2866-43-5

Structure of FBA 185
CAS No.: 2866-43-5

Chemical Structure| 2866-43-5

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Product Details of [ 2866-43-5 ]

CAS No. :2866-43-5
Formula : C18H10N2O2S
M.W : 318.35
SMILES Code : C1(C2=NC3=CC=CC=C3O2)=CC=C(C4=NC5=CC=CC=C5O4)S1
English Name :2,5-Bis(benzo[d]oxazol-2-yl)thiophene
MDL No. :MFCD00205000

Safety of [ 2866-43-5 ]

Application In Synthesis of [ 2866-43-5 ]

* 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 [ 2866-43-5 ]

[ 2866-43-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1388433-19-9 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
at 200℃; for 3h; Yield given;
YieldReaction ConditionsOperation in experiment
Thiophene-2,5-dicarboxylic acid, entspr. o-NH2-Phenol;
2-Amino-phenol I, Thiophen-2,5-dicarbonsaeure II;
entspr. Tetrahydrothiophen;
2-Amino-phenol, 2,5-Thiophendicarbonsaeure;
aus Butan 1 m. S;
Thiophen-2,5-dicarbonsaeure, entspr. Aminophenol;
Tetrahydrothiophen(I,R=H,X=O),FeCl3;
Glyoxal, entspr. Bismethylthioether, Cycl.;
entspr. Aldimin;
Dichlortetrahydrothiophen-2,5-dicarbonylchlorid/o-Aminophenol;
2,5-Thiophendicarbonsaeure, o-Hydroxyanilin;
durch Oxyd. entspr.Tetrahydrothiophenderivat III;

  • 3
  • [ 273-53-0 ]
  • [ 3141-27-3 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
51% With [PdCl(dppb)(C3H5)]; caesium carbonate In N,N-dimethyl-formamide at 150℃; for 20h; Inert atmosphere; regioselective reaction;
  • 4
  • [ 3857-36-1 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Heating 2: 3 h / 200 °C
  • 5
  • [ 4282-31-9 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-methyl-2-pyrrolidone, thionyl chloride 2: Heating 3: 3 h / 200 °C
  • 6
  • [ 4282-31-9 ]
  • [ 95-55-6 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
89.23% With boric acid; tin(ll) chloride In 1,2-dichloro-benzene at 220℃; for 24h; Inert atmosphere; Dean-Stark; 1 Comparative Example 1: Synthesis of Comparative Compound After dissolving 2,5-thiophenedicarboxylic acid (10g, 58mmol, 1eq) and 2-amino phenol (17.781g, 159mmol, 2.75eq) in a reactor under a nitrogen atmosphere in 1,2-dichlorobenzene (67ml), boric acid ( 1.1 g, 17 mmol, 0.3 eq) and stannous chloride (1.3 g 6 mmol, 0.1 eq) were added. After installing the Dean Stark apparatus, the mixture was stirred and heated at a temperature of 220° C. for 24 hours. After the reaction was completed, the 1,2-dichlorobenzene remaining in the reactor was removed by distillation under reduced pressure, dimethylformamide was added to the reactor, heated and cooled, and then filtered under reduced pressure to obtain a comparative compound of solid phase (16.5 g, Yield=89.23%)
89.23% With tin(ll) chloride In 1,2-dichloro-benzene at 220℃; for 24h; Inert atmosphere; Dean-Stark; Comparative Example: Synthesis of Comparative Compound 2,5-thiophenedicarboxylic acid (10g, 58mmol, 1eq) and 2-aminophenol (17.781g, 159mmol, 2.75eq) were dissolved in 1,2-dichlorobenzene (67ml) in a reactor under a nitrogen atmosphere, and then boric acid ( 1.1g, 17mmol, 0.3eq) and stannous chloride (1.3g 6mmol, 0.1eq) were added. After that, after installing the Dean-Stark device, it is stirred and heated at a temperature of 220° C. for 24 hours. After the reaction was completed, the 1,2-dichlorobenzene remaining in the reactor was removed by distillation under reduced pressure, dimethylformamide was added to the reactor, heated and cooled, and then filtered under reduced pressure to obtain a solid comparative compound. (16.5 g, yield = 89.23%)
5.5% Stage #1: Thiophene-2,5-dicarboxylic acid; 2-amino-phenol at 150℃; for 2h; Inert atmosphere; Stage #2: With ammonia In water at 20℃; Cooling with cold water; 1.5 A solution of amino compound (XV) (5.8 mmoles) and 2,5- thiophenedicarboxylic acid (5.8 mmoles) in PPA (10 ml) was stirred under N2 atmosphere at 150° C for 2h. Cooled the reaction mass to RT, poured into cold water, neutralized with ammonia solution to pH~ 10-1 1, then extracted with ethyl acetate, washed with brine followed by water, dried the organic layer over anhydrous Na2SO4 and distilled to give the crude product, which was then purified by using silica gel 60-120 mesh column chromatography and DCM: methanol 100-5 % as mobile phase to get the pure compound (XX). Table 11: preparation of thiophene benzimidazole dimer (XX).
With boric acid In 1-methyl-pyrrolidin-2-one; toluene at 20 - 185℃; for 13h; 4 200 g of N-methylpyrrolidone are charged to a reaction vessel and 52 g of 98% thiophene-2,5-dicarboxylic acid, followed by 72 g of 99% 2-aminophenol, 10 g of boric acid and 30 g of toluene are added with stirring. The apparatus, equipped with a Dean and Stark water trap, is evacuated and the vacuum released with nitrogen. The light yellow suspension is heated to 185[deg.] C. and stirred at this temperature for 12 hours, during which time 23-25 ml of water and approximately 25 g of toluene are distilled off through the water trap. The reaction mixture is cooled to 20[deg.] C. and stirring continued for 1 hour at this temperature. The yellow suspension is filtered, washed with 100 g of N-methylpyrrolidone to give 300 g of a brown solution which may be used as solvent for a further charge and then with three 80 g portions of water. The resulting press-cake is dried under a vacuum of 50 mbar at 100[deg.] C. to yield 75 g of the compound of formula (104) as a yellow solid, characterized by a UV absorption maximum [lambda]max at 372 nm with an extinction coefficient [epsilon] of 52000 and by the following <1>H-NMR data in D6-DMSO: [0045] 8.10, 2H, s; 7.82, 4H, m and 7.50, 4H, m.

  • 7
  • [ 273-53-0 ]
  • [ 3141-27-3 ]
  • [ 934329-17-6 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
51% With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 20h;
  • 8
  • [ 273-53-0 ]
  • [ 625-88-7 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
89% With [Pd(1,10-phenanthroline)2](PF6)2; caesium carbonate In dimethyl amine at 150℃; for 20h; Inert atmosphere;
  • 9
  • [ 2866-43-5 ]
  • [ 2596196-15-3 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; nitric acid at 0℃; for 1h;
  • 10
  • [ 932-95-6 ]
  • [ 88-75-5 ]
  • [ 16155-56-9 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
1: 63% 2: 21% Stage #1: 2,5-thiophenedicarboxaldehyde; 2-hydroxynitrobenzene In 1,4-dioxane; water at 100℃; for 0.0833333h; Stage #2: With formic acid In 1,4-dioxane; water at 100℃; for 8h; Sealed tube;
  • 11
  • [ 273-53-0 ]
  • [ 3172-52-9 ]
  • [ 2866-43-5 ]
YieldReaction ConditionsOperation in experiment
74% With potassium phosphate; C37H38FeO6P2Pd In butan-1-ol at 125℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;
 

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