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[ CAS No. 22162-53-4 ] {[proInfo.proName]}

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Chemical Structure| 22162-53-4
Chemical Structure| 22162-53-4
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Product Details of [ 22162-53-4 ]

CAS No. :22162-53-4 MDL No. :MFCD02093091
Formula : C12H12N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 184.24 Pubchem ID :-
Synonyms :

Safety of [ 22162-53-4 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22162-53-4 ]

* 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 [ 22162-53-4 ]

[ 22162-53-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 181074-22-6 ]
  • [ 79-37-8 ]
  • [ 117738-77-9 ]
  • [ 22162-53-4 ]
  • [ 220461-91-6 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; hexane; dichloromethane; ethyl acetate; EXAMPLE 77 3-Chloro-4-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-benzonitrile To a cooled suspension of <strong>[117738-77-9]2-chloro-4-cyanobenzoic acid</strong> (9.1 g) in a mixture of dichloromethane (40 ml) and dimethylformamide (3.88 ml) was added dropwise a solution of oxalyl chloride (4.6 ml) in dichloromethane (10 ml) at 0 C. The stirred reaction was allowed to warm to room temperature over a one hour period. A cloudy solution of 2-chloro-4-cyanobenzoyl chloride was utilized without further purification. To a stirred suspension of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (7.32 g) and diisopropylethylamine (13.6 ml) in dichloromethane (35 ml) was added under nitrogen the cloudy solution of 2-chloro-4-cyanobenzoyl chloride. After one hour at room temperature, the mixture was diluted with dichloromethane and washed sequentially with water, 5% sodium bicarbonate, and 50% saturated brine, After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to afford a crude product (18.0 g). Purification by column chromatography on silica gel (250 g), eluding with 20% ethyl acetate/hexane, followed by 25% ethyl acetate/hexane, yielded the title compound (13.56 g) as a straw yellow foam, MS (EI), m/z: 347 (M)+.
  • 2
  • [ 544-00-3 ]
  • [ 725-14-4 ]
  • [ 22162-53-4 ]
  • [ 473717-56-5 ]
YieldReaction ConditionsOperation in experiment
86.8% In thionyl chloride; hexane; dichloromethane; ethyl acetate; toluene; Step C. (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone A suspension of the carboxylic acid of Step B (1.0 g, 4.38 mmol) in thionyl chloride (6 mL) was heated at reflux for 1 hour. After cooling, the thionyl chloride was removed in vacuo. The residue was dissolved in toluene and concentrated in vacuo to give the crude acid chloride as a light brown solid. The acid chloride was then dissolved in dichloromethane (10 mL) and slowly added to a solution of 10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine (1.2 g, 6.52 mmol) and N,N-diisopropylethyl amine (1.7 mL, 9.76 mmol) in dichloromethane (25 mL). After stirring for 2 hours, the reaction was quenched with water. The organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow foam. Purification of the residue by flash chromatography using a solvent gradient from 15% to 50% of ethyl acetate in hexane provided the title compound (1.5 g, 86.8%) as a white solid, m.p. 187-189 C. 1H-NMR (DMSO-d6, 400 MHz): δ 3.76 (s, 3H), 4.80-5.40 (broad s, 4H), 5.92-5.94 (m, 1H), 5.96 (s, 1H), 6.83 (t, 1H), 6.94-6.99 (m, 3H), 7.10 (t, 1H), 7.15-7.19 (m, 1H), 7.32 (d, 2H), 7.47-7.49 (m, 3H), 7.55-7.58 (m, 2H). MS [(+)ESI, m/z]: 395 [M+H]+. Anal. Calcd. for C26H99N2O2+0.20CH2Cl2: C, 76.48; H, 5.49; N, 6.81. Found: C, 76.10; H, 5.68; N, 6.87.
  • 3
  • [ 79-37-8 ]
  • [ 141179-72-8 ]
  • [ 22162-53-4 ]
  • [ 220461-64-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; hexane; dichloromethane; EXAMPLE 1 (4-Fluoro-2-trifluoromethyl-phenyl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone Oxalyl chloride (2.0 g) was added to a suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (2.0 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to give the crude acid chloride. This was redissolved in dichloromethane and filtered. Evaporation of this material gave a liquid which was then redissolved in hexane, filtered, and evaporated to yield the acid chloride as a pale yellow viscous liquid, which was used without further purification. The acid chloride (2.26 g) in dichloromethane (25 ml) was added portionwise to a mixture of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.66 g), dichloromethane (10 ml), and diisopropylethylamine (1.30 g), cooled in an ice bath. After remaining at room temperature for 18 hours, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield 2.57 g of the title compound, m.p. 154-155 C.
  • 4
  • [ 69535-85-9 ]
  • [ 22162-53-4 ]
  • [ 909040-95-5 ]
YieldReaction ConditionsOperation in experiment
A solution of 0.45 g (0.002 mole) of <strong>[69535-85-9]2,2'-dimethyl-1,1'-biphenyl-4-carboxylic acid</strong> in 50 mL of thionyl chloride was heated under reflux overnight. The excess thionyl chloride was stripped off in vacuo. To the residue was added 0.37 g (0.002 mole) of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 50 mL of 1,4-dioxane followed by 0.24 g (0.002 mole) of N,N-dimethylaniline. After standing for three hours, the reaction solution was poured into 300 mL of water to provide 0.6 g of title compound which was used directly in the next step after drying. MS [(+)ESI, m/z]: 393 [M+H]+.
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