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[ CAS No. 5044-23-5 ] {[proInfo.proName]}

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Chemical Structure| 5044-23-5
Chemical Structure| 5044-23-5
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Product Details of [ 5044-23-5 ]

CAS No. :5044-23-5 MDL No. :MFCD00027420
Formula : C12H12ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 205.68 Pubchem ID :-
Synonyms :

Safety of [ 5044-23-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5044-23-5 ]

* 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 [ 5044-23-5 ]

[ 5044-23-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5044-23-5 ]
  • [ 79-04-9 ]
  • [ 571159-05-2 ]
YieldReaction ConditionsOperation in experiment
39.9% Stage #1: chloroacetyl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.5h; Stage #2: 1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrole In 1,2-dichloro-ethane at 0 - 20℃; for 2h; 1 To a solution of A1C13 (7.98 g, 60.0 mmol) in 1, 2-dichloroethane (50 mL) was added Id (6.78 g, 60.0 mmol) at 0 °C. The resulting mixture was stirred for 30 min and added to a solution of lc (6.17 g, 30.0 mmoL) in 1 , 2-dichloroethane (50 mL) at 0 °C. The reaction mixture was then warmed to room temperature for 2 hour and poured into ice- water (20 mL). The mixture was extracted with dichloromethane (15 mL x 3), dried over MgS04 and purified by silica column chromatography to give le, 3.37 g, yield: 39.9%
39.9% Stage #1: chloroacetyl chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 0℃; for 0.5h; Stage #2: 1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrole In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Synthesis of compound 3 2-Chloroacetyl chloride (6.78 g; 60.0 mmol) was added to asuspension of AlCl3 (7.98 g; 60.0 mmol) in 1,2-dichloroethane (50 ml) at 0 °C. The resulting mixture was stirred for 30 min and was then added to a solution of compound 2 (6.17 g; 30.0 mmol)in 1,2-dichloroethane (50 ml) at 0 °C. The reaction mixture was then allowed to warm to room temperature and stirred for 2 h.The mixture was poured into ice-water (20 ml) and extracted with dichloromethane (3 15 ml). The combined organic layerswere dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to affordthe title compound (3.37 g; yield, 39.9%).
30% Stage #1: 1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrole; chloroacetyl chloride With aluminum (III) chloride In dichloromethane at 0℃; for 2h; Stage #2: With water In dichloromethane Cooling with ice; 5 Synthesis of 2-chloro-1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)ethanone (A8) Example 5 Synthesis of 2-chloro-1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)ethanone (A8) 2-chloro-1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)ethanone (A8): Aluminum chloride (7.42 g, 55.6 mmol) was placed in a dry flask and 10 mL of dry CH2Cl2 was added. The reaction cooled to 0° C. and 2-chloro-acetyl chloride (4.42, 55.6 mmol) was added. Pyrrole (1) (7.18 g, 34.8 mmol) was placed in a flask and taken up in 20 mL dry CH2Cl2. The solution was cooled to 0° C. After 1.5 hours the acid chloride mixture was added to the pyrrole solution. After stirring at 0° C. for 30 min. the reaction was poured onto ice. After the ice melted the layers were separated and the aq. phase was extracted twice with CH2Cl2. The combined layers were washed with brine, dried over MgSO4 and adsorbed onto silica gel. The material was purified using silica gel chromatography (95:5 hexanes:EtOAc). Chloride (A8) was isolated as a white 1H NMR (300 MHz, CDCl3) δ ppm 7.49 (m, 2H), 7.13 (m, 2H), 6.30 (s, 1H), 4.47 (s, 2H), 2.31 (s, 3H), 1.99 (s, 3H); low resolution mass spectrum (ES+) m/z 281.94 [(M+H+); calcd for C14H13Cl2NO+H 282.04]. solid (3.11 g, 10.5 mmol, 30% yield).
  • 2
  • [ 110-13-4 ]
  • [ 100-00-5 ]
  • [ 5044-23-5 ]
YieldReaction ConditionsOperation in experiment
94% With indium; acetic acid In toluene at 80℃; for 6h; Inert atmosphere; 12 4.2.12. 1-(4-Chlorophenyl)-2,5-dimethyl-1H-pyrrole (14).5j General procedure: Nitrobenzene derivative (1.0mmol) was added to a mixture of indium powder (460mg, 4.0mmol), and acetic acid (0.572mL, 10mmol) in toluene (2mL), followed by the addition of 2,5-hexadione or 1-phenyl-1,4-pentanedione (1.0mmol) in toluene (3mL). The reaction mixture was stirred at 80°C for 2,5-hexadione (or reflux for 1-phenyl-1,4-pentadione) under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30mL), filtered through Celite, poured into 10% NaHCO3 (30mL), and then extracted with ethyl acetate (30mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with hexane for most derivatives or ethyl acetate/hexane (v/v=5:95) for benzonitrile derivatives through a neutral silica gel column to give the corresponding pyrroles. The structures of the pyrroles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. If it is an unknown compound, elemental analysis data were reported additionally.
93.9% With formic acid for 12h; Autoclave; Inert atmosphere; Green chemistry;
82 %Chromat. With hydrogen In methanol at 100℃; for 24h;
  • 3
  • [ 5044-23-5 ]
  • [ 54322-65-5 ]
  • 1-(1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-cyclopropylethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
35.7% With zinc; In toluene; at 25℃; for 2.5h; Cyclopropylacetyl chloride (1.17 g, 9.92 mmol) was added to a stirred solution of 1 -(4-chlorophenyl)-2,5-dimethyl-1H-pyrrole (prepared according to the procedure given in Synthetic Communications, 2009, 39, 23, 4180-4198) (1.70 g, 8.27 mmol) and Zinc (1.08 g, 16.53 mmol) in toluene (15 ml) at 25 C. The reaction mixture was stirred at 25 C for 2.5 h. The progress of the reaction was monitored by TLC. The mixture was diluted with saturated solution of sodium bicarbonate (30 ml), and the resulting aqueous and organic phases were separated. The aqueous layer was extracted with ethyl acetate (3 x 50 ml). Thecombined organic layer was washed with water (1 x 30 ml) and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain a crude product. This crude product was purified by column chromatography using 10% ethyl acetate in hexanes as an eluent to obtain compound 1a (0.85 g, 35.7%). MS: m/z 288 (M+1). 1H NMR (CDCl3, 400 MHz): δ 7.49 (d, J 8.4 Hz, 2H), 7.14 (d, J = 8.4 Hz, 2H), 6.30 (s, 1H), 2.67 (d, J 6.8 Hz, 2H), 2.34 (s, 3H), 1.97 (s, 3H), 1.16- 1.20 (m, 1H), 0.56-0.61 (m, 2H), 0. 18-0.22 (m, 2H).
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