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[ CAS No. 26165-66-2 ]

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Chemical Structure| 26165-66-2
Chemical Structure| 26165-66-2
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Product Details of [ 26165-66-2 ]

CAS No. :26165-66-2 MDL No. :MFCD01125267
Formula : C14H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :229.27 g/mol Pubchem ID :-
Synonyms :

Safety of [ 26165-66-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26165-66-2 ]

  • Downstream synthetic route of [ 26165-66-2 ]

[ 26165-66-2 ] Synthesis Path-Downstream   1~16

YieldReaction ConditionsOperation in experiment
41% With Hf/SBA-15(20) at 150℃; for 6h; Inert atmosphere; 28 Example 1 General procedure: Put 140 mg Hf/SBA-15(20) (that is, the Si/Hf ratio is 20),1.5 mL 2,5-dimethylfuran,0.5 mmol aniline into the pressure tube,The molar ratio of hafnium metal to aniline in the catalyst is 18.2%,Under the atmosphere of N2 protection, the reaction was carried out at 150°C with a stirring speed of 800 rpm for 6 hours,The reaction product was confirmed by nuclear magnetic analysis that the main product was indeed 2,5-dimethyl-1-phenyl-1H-pyrrole, as shown in Figure 1.With naphthalene as an internal standard, the yield of 2,5-dimethyl-1-phenyl-1H-pyrrole was 97.3% by gas chromatography quantitative analysis.
Entspr. Saeure, ROH;
  • 2
  • [ 26165-66-2 ]
  • [ 26165-67-3 ]
YieldReaction ConditionsOperation in experiment
85% With hydrazine hydrate In ethanol Reflux; 3.2.4. 4-(2,5-Dimethyl-1H-pyrrol-1-yl)benzoic acid hydrazide (18) A mixture of methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate (16) (2.29 g, 10 mmol) and hydrazine hydrate(2.25 g, 45 mmol) in 96% ethanol (10 mL) was heated at reflux temperature overnight. The solid that separatedon cooling was filtered and recrystallized to give colorless crystals (1.95 g, 85%), mp 164-165 °C (ethanol) (lit.35mp 148 °C); 1 H NMR (DMSO-d6 , 400 MHz): 1.97 (s, 6H), 4.54 (s, 2H, exchangeable with D), 5.81 (s, 2H),7.34 (d, J = 8.4 Hz, 2H), 7.94 (d, J = 8.4 Hz, 2H), 9.89 (s, 1H, exchangeable with D); 13 C NMR (DMSO-d6 ,100 MHz): 12.9, 106.4, 127.5, 127.8, 128.0, 132.4, 140.6, 165.2. Anal. Calcd. for C13 H15 N3 O: C, 68.10; H,6.59; N, 18.33. Found: C, 68.25; H, 6.71; N, 18.48.
With hydrazine hydrate In ethanol for 1h; Reflux;
  • 4
  • [ 110-13-4 ]
  • [ 619-45-4 ]
  • [ 26165-66-2 ]
YieldReaction ConditionsOperation in experiment
98% With MIL-53(Al) In neat (no solvent) at 80℃; for 0.25h; Sonication;
96% With Cl(1-)*C5H14NO(1+)*3ZnCl2 In neat (no solvent) for 0.166667h; Sealed tube; Sonication; Green chemistry;
84% With 1-allyl-3-methylimidazolium tetrafluoromethanesulfonate; zinc(II) chloride at 80℃; for 1h; Sonication; General procedure for Paal-Knorr reaction General procedure: A solution of aniline (1 mmol, 0.094 g), acetonylacetone (1.2 mmol, 0.136 g) and ZnCl2(10 mol%, 0.0136 g) in the presence of [AMIm](OTf) (0.1 g) was sonicated at 80 C for the appropriate time indicated. The completion of the reaction was monitored by thin layer chromatography (TLC) and GC. The reaction mixture was extracted with diethylether (10 x 5 mL). The combined organic extract was washed with water (10 mL), dried with anhydrous sodium sulfate, filtered and dried under vacuum at 30 C. The residue was purified by chromatography on silica gel using ethyl acetate-hexane (1:9). The product was characterized by 1H and 13C NMR.
81% With toluene-4-sulfonic acid In toluene at 150℃; for 1h; Sealed tube; Microwave irradiation;
75% In ethanol; acetic acid for 6h; Reflux; 3.2.2. Methyl 4-(2,5-dimethyl-1H-pyrrol-1-yl)benzoate (16) A solution of methyl 4-aminobenzoate (3.02 g, 20 mmol), 2,5-hexanedione (2.28 g, 20 mmol), and glacial acetic acid (0.5 mL) in 96% ethanol (20 mL) was heated at reflux temperature for 6 h, and then the solvent was partially removed under reduced pressure. The solid that separated on cooling was filtered and recrystallized from 2-propanol to give tan crystals (3.44 g, 75%), mp 92-93 °C (lit.35 mp 88 °C); 1 H NMR (DMSO-d6 , 400MHz): 1.99 (s, 6H), 3.89 (s, 3H), 5.84 (s, 2H), 7.43 (d, J = 8.8 Hz, 2H), 8.07 (d, J = 8.8 Hz, 2H); 13 CNMR (DMSO-d6 , 100 MHz): 12.9, 52.3, 106.7, 127.5, 128.2, 128.6, 130.2, 142.5, 165.7. Anal. Calcd. forC14 H15 NO2 : C, 73.34; H, 6.59; N, 6.11. Found: C, 73.24; H, 6.51; N, 6.03.

  • 5
  • [ 26165-66-2 ]
  • [ 619-45-4 ]
YieldReaction ConditionsOperation in experiment
72% With hydrogenchloride In methanol at 120℃; for 0.333333h; Microwave irradiation;
  • 6
  • [ 109-49-9 ]
  • [ 619-45-4 ]
  • [ 26165-66-2 ]
YieldReaction ConditionsOperation in experiment
76% With palladium(II) trifluoroacetate; oxygen In toluene at 100℃; General procedure for the preparation of pyrroles 3. General procedure: All the reactions were carried out under aerobic atmosphere. To a solution of substrate 5-hexen-2-one 1 (0.6 mmol, 1.2 mmol for the diamines substrates) and amines 2 (0.5 mmol) in toluene (2.0 mL) was added to Pd(OCOCF3)2 (0.05 mmol, 16.5 mg). The mixture with O2 balloon was stirred at 100 °C overnight. The substrate was consumed completely monitored by TLC. The mixture was cooled to room temperature, filtered through celite, washed with ethylacetate and concentrated under vacuum. The resulting residue was purified by column chromatography using hexane/ethyl acetate (v/v, 20/1 to 10/1) as the eluent to give the desired product.
  • 7
  • [ 26165-66-2 ]
  • 4-allyl-3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-1H-1,2,4-triazole-5-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux
  • 8
  • [ 26165-66-2 ]
  • 3-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4-phenyl-1H-1,2,4-triazole-5-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux
  • 9
  • [ 26165-66-2 ]
  • ethyl 2-{{4-allyl-5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4H-1,2,4-triazol-3-yl}thio}acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: potassium carbonate / butanone / 6 h / Reflux
  • 10
  • [ 26165-66-2 ]
  • ethyl 2-{{5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4-phenyl-4H-1,2,4-triazol-3-yl}thio} acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: potassium carbonate / butanone / 6 h / Reflux
  • 11
  • [ 26165-66-2 ]
  • 4-allyl-3-[(3,4-dichlorobenzyl)thio]-5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: potassium hydroxide / ethanol / 1 h / Reflux
  • 12
  • [ 26165-66-2 ]
  • 3-[(4-chlorobenzyl)thio]-5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4-phenyl-4H-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: potassium hydroxide / ethanol / 1 h / Reflux
  • 13
  • [ 26165-66-2 ]
  • 1-(4-chlorophenyl)-2-{{5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-4-phenyl-4H-1,2,4-triazol-3-yl}thio}ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: potassium hydroxide / ethanol / 1 h / Reflux
  • 14
  • [ 26165-66-2 ]
  • 4-allyl-5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-2-(morpholinomethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: ethanol; water / 1 h / Reflux
  • 15
  • [ 26165-66-2 ]
  • 4-allyl-5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-2-(piperidin-1-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: ethanol; water / 1 h / Reflux
  • 16
  • [ 26165-66-2 ]
  • 5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)phenyl]-2-(morpholinomethyl)-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrazine hydrate / ethanol / Reflux 2: ethanol / 1 h / Reflux 3: potassium hydroxide / water / 3 h / Reflux 4: ethanol; water / 1 h / Reflux
Historical Records

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