[ CAS No. 10242-12-3 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 10242-12-3
Chemical Structure| 10242-12-3
Structure of 10242-12-3

Quality Control of [ 10242-12-3 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 10242-12-3 ]

SDS

Product Details of [ 10242-12-3 ]

CAS No. :10242-12-3MDL No. :MFCD00060513
Formula :C9H5NO5Boiling Point :-
Linear Structure Formula :-InChI Key :N/A
M.W :207.14Pubchem ID :-
Synonyms :

Computed Properties of [ 10242-12-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 10242-12-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H302-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10242-12-3 ]

  • Downstream synthetic route of [ 10242-12-3 ]

[ 10242-12-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 10242-12-3 ]
  • [ 413577-26-1 ]
  • [ 413577-33-0 ]
YieldReaction ConditionsOperation in experiment
22% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 48h; The achiral 2-(4-benzyloxy-2-nitrophenyl)ethyl chloride compound (0.500 g, 1.71 mmol) was dissolved in freezer-chilled THF (30 mL) and PtO2 (0.150 g) was added. The reaction was stirred while degassing under vacuum, followed by exposure to hydrogen gas. The degas/hydrogen exposure cycle was repeated 3 times, at which point the reaction was allowed to continue stirring under hydrogen at 50 psi at room temperature for one hour. The amine solution was filtered over Celite, and concentrated under reduced pressure. It was then coevaporated three times with dry CH2Cl2 (5 mL). A tan oil resulted and was placed under high vacuum, covered with foil for 30 minutes. Then, [10242-12-3]5-nitrobenzofuran-2-carboxylic acid (0.394 g, 1.90 mmol) and PyBOP (0.999 g, 1.92 mmol) were suspended in dry CH2Cl2 (220 mL). The amine was then dissolved in dry CH2Cl2 (30 mL) and added to the suspension via a syringe through a septum. The reaction was allowed to stir for 10 minutes, at which point dry N,N-Diisopropylethylamine (0.75 mL, 4.29 mmol) was added to the suspension. The solution turned clear yellow. It was covered with foil and the solution was stirred under nitrogen, at room temperature for two days. The solution was vacuum filtered and the filtrate was washed with water (1×75 mL), 10% HCl (1×75 mL), saturated Sodium bicarbonate (1×75 mL), and brine (1×75 mL). The organic layer was dried over sodium sulfate, vacuum filtered, and concentrated under reduced pressure to yield a yellow solid. The residue was purified on a silica gel column using a 5-20% EtOAc/hexane solvent system to give the desired product 2-(4-benzyloxy-2-(5-nitrobenzofuran-2-carboxamido)phenyl)ethyl chloride as a yellow solid (0.173 g, 22% yield). Rf=0.22 (20% EtOAc/hexane) M.p. 109-113 C. IR (neat) 3370, 3088, 3032, 2945, 2858, 1690, 1531, 1337, 1270, 1168, 1101, 1025, 753, 610 1H-NMR (500 MHz, CDCl3) 8.67 (d, 2.0, 1H), 8.64 (s br, 1H), 8.39 (dd, 2.0, 9.0, 1H), 7.73 (s, 1H), 7.70 (d, 9.0, 1H), 7.65 (d, 2.5, 1H), 7.45 (d, 8.0, 2H), 7.40 (t, 8.0, 2H), 7.36 (t, 8.0, 1H), 7.19 (d, 8.5, 1H), 6.89 (dd, 2.5, 8.5, 1H), 5.10 (s, 2H), 3.83 (t, 6.5, 2H), 3.14 (t, 6.5, 2H). FAB-MS (NBA) 451 (M+H+, 11). Accurate mass for C24H19N2O5Cl+H: calcd. 451.1060; obs. 451.1050.
  • 2
  • [ 10242-12-3 ]
  • [ 351890-37-4 ]
  • [ 489457-57-0 ]
  • 3
  • [ 10242-12-3 ]
  • [ 90036-16-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 40℃; for 3.5h; 5-Nitroglycerine benzofuran 2-carboxylic acid (14) (1.0 g, 4.8 mmol) was dissolved in methylene chloride (10 mL). Thionyl chloride (1.15 mL, 1.58 mmol) and N,N-dimethylformamide (30 muL) were added, and the resultant solution was stirred at 40 C for 3.5 h. After cooling in air, the mixture was concentrated under reduced pressure. The residue was dissolved in THF (10 mL). Triethylamine (1.0 mL, 7.2 mmol) and tert-butyl-carbazate (0.77 g, 5.8 mmol) were then added, and the resultant solution was stirred at 0 C for 1 h. Water was added to the reaction mixture, followed by ethyl acetate. The organic layer was dried with anhydrous sodium sulfate.CommentThe combined organic solutions were filtered, and concentrated under reduced pressure. The resultant solid was washed with ethyl acetate/hexane to give compound 15 (1.3 g, 4.1 mmol, 85% yield).
With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 70 - 115℃; for 0.5h; Toluene (1200 ml) and [10242-12-3]5-nitrobenzofuran-2-carboxylic acid of Formula (C) were added to a four-neck two litre round bottom flask at 35 C. and stirred for 15 minutes. DMF (10 ml) was added and heated to 70 C. followed by addition of Thionyl chloride (86.4 g) and heated to 115 C. and maintained for 30 minutes. Toluene was distilled out and reaction mass was cooled to 35 C. and further cooled to 10 C. Ammonia gas was passed till pH was 8 to 9. The product was washed with Toluene (2*100 ml) and dried for 60 minutes and dried in hot air oven at for 12.0 hrs at 65 C. To the obtained product DMF (250 ml) was added at 35 C. and heated to 130 C. The reaction mass was stirred for 30 minutes and cooled to 95 C. followed by addition of water (2300 ml) and stirred for 30 minutes. The reaction mass was cooled to 50 C. The product was filtered and washed with water (2*100 ml) to afford 5-nitrobenzofuran-2-carboxamide of Formula (D).
  • 4
  • [ 10242-12-3 ]
  • [ 530-62-1 ]
  • imidazol-1-yl-(5-nitro-benzofuran-2-yl)-methanone [ No CAS ]
  • 6
  • [ 10242-12-3 ]
  • [ 100-46-9 ]
  • 5-amino-benzofuran-2-carboxylic acid benzylamide [ No CAS ]
  • 7
  • [ 685-87-0 ]
  • [ 97-51-8 ]
  • [ 10242-12-3 ]
  • [ 69604-00-8 ]
  • 8
  • 2-formyl-<4-nitro-phenoxy>-acetic acid [ No CAS ]
  • [ 10242-12-3 ]
  • 10
  • [ 10242-12-3 ]
  • [ 124-40-3 ]
  • N,N-dimethyl-5-nitrobenzofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Compound 1 (300 mg) and HATU (551 mg) were dissolved in DMF (10 mL),DIEA (561 mg) was added dropwise thereto, and after stirring at room temperature for 15 minutes,Dimethylamine (2.2 mL, 2.0 M in THF) was then added to the reaction system.Stir for 20 hours at room temperature, dilute with saturated ammonium chloride solution, extract with ethyl acetate,The combined organic phases were dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure,The obtained residue 2 (crude, 320 mg) was used directly in the next reaction.
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