Home Cart 0 Sign in  

[ CAS No. 25084-14-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 25084-14-4
Chemical Structure| 25084-14-4
Structure of 25084-14-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 25084-14-4 ]

Related Doc. of [ 25084-14-4 ]

Alternatived Products of [ 25084-14-4 ]

Product Details of [ 25084-14-4 ]

CAS No. :25084-14-4 MDL No. :MFCD00039564
Formula : C5H2ClNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 175.53 Pubchem ID :-
Synonyms :

Safety of [ 25084-14-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 25084-14-4 ]

* 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 [ 25084-14-4 ]

[ 25084-14-4 ] Synthesis Path-Downstream   1~46

  • 1
  • [ 25084-14-4 ]
  • [ 144-80-9 ]
  • 5-nitro-furan-2-carboxylic acid-(4-acetylsulfamoyl-anilide) [ No CAS ]
  • 2
  • [ 645-12-5 ]
  • [ 25084-14-4 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 3h; To an ice cold solution of 5-nitrofuran-2- carboxylic acid (450 mg, 2.90 mmol) in DCM (10 ml) oxalyl chloride (2.50 L, 29 mmol) was added followed by addition of catalytic amount of DMF at 0 C and the reaction mixture was allowed to stir for 3h at room temperature. On completion, the solvent was evaporated under reduced pressure toobtain the acid chloride A with a quantitative yield (498 mg).
99% With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 4h; <strong>[645-12-5]5-Nitro-2-furoic acid</strong> (7a, 1.5 g, 9.4 mmol) was partly dissolved in 20 mL of dry dichloromethane. Oxayl chloride (1.8 mL, 21.3 mmol) was added followed by a few drops of DMF. The reaction was stirred for 4 hours then concentrated to dryness in vacuo to give intermediate acid chloride, 8a, as yellow oil which became solid upon standing, 1.0 g (99%). 5-Nitrofuran-2-carbonyl chloride (8a, 624 mg, 3.5 mmol) was dissolved in 10 mL of anhydrous dichloromethane and the solution was cooled to 0 C. 2-Aminophenol (9, 460 mg, 4.2 mmol) was added followed by Et3N (1.4 mL, 10.5 mmol) and the reaction was then allowed to warm to room temperature and stirred overnight. The reaction was concentrated to dryness in vacuo then diluted with EtOAc (75 mL) and washed with 0.5 N citric acid (2×), 10% sodium bicarbonate soln. (2×) and then satd. brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to give a yellow film. The residual material was triturated with dichloromethane and upon cooling a yellow solid of N-(2-hydroxyphenyl)-5-nitrofuran-2-carboxamide, 10a, was collected, 631 mg (73%). HRMS calcd. for C11H8N2O5, 249.0511 found 249.0517. N-(2-Hydroxyphenyl)-5-nitrofuran-2-carboxamide (10a, 151 mg, 0.6 mmol) was dissolved in 6 mL of toluene containing p-toluenesulfonic acid, monohydrate (700 mg, 3.7 mmol) and the reaction was heated to reflux overnight. The reaction was concentrated in vacuo then purified through a silica gel column eluting with dichloromethane and increasing polarity to 10% EtOAc:dichloromethane to collect product 11a as a yellow-green solid, 62 mg (44%). 1H NMR (300 MHz, CDCl3) delta 7.87-7.81 (1H, m), 7.67-7.62 (1H, m), 7.46 (4H, m); HRMS calcd. for C11H6N2O4, 231.0406 found 231.0423. LC/MS Retention time 7.53 min (<95%), FABMS 231.3 (M+1).
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h; 5-Nitro-furan- 2-carboxylic acid (942 mg, 6 MMOL) in DCM (10 mL) was treated with oxalylchloride (1.046 mL, 12 MMOL) followed by 2 drops of DMF and stirred at room temperature for 4 hr. The reaction mix was concentrated in vacuum to obtain acid chloride.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h; 5-NITRO-FURAN-2-CARBOXYLIC acid (942 mg, 6 MMOL) in DCM (10 mL) was treated with oxalylchloride (1.04 mL, 12 MMOL) followed by 2 drops of DMF and stirred at room temperature for 4 hrs. The reaction mix was concentrated in vacuum to obtain acid chloride and the crude was used in further reactions without purification and characterization.
General procedure: 5-Nitrothiophene-2-carboxylic acid (2.0g) was taken in a 100mL single neck RB flask equipped with N2-inlet, to this was added CH2Cl2 (30mL), OxallylChloride (6.0mL, 3V) at 0C and stirred for few minutes. Then DMF (few drops) was added slowly (drop wise) at same temperature until evolution of bubbles in the reaction mixture was stopped, and allowed to stir at room temperature for 3h. The reaction mixture was concentrated re-dissolved in dry CH2Cl2 and used in next step.
With thionyl chloride; for 1h;Reflux; A stirred mixture of 5-nitrofuroic acid (5-NFA 100mg; 0.64mmol) and SOCl2 (3mL) was refluxed in a silicone bath for 1h until gas evolution stops. The reaction mixture was left to take room temperature and, with the addition of anhydrous toluene (1mL), the excess of SOCl2 was evaporated in vacuo. Then, a solution of selected amine (0.86mmol in 0.5mL of anhydrous pyridine) was dropwise added to the acid chloride (obtained as oil) dissolved in anhydrous acetone (2.2mL) and the mixture was maintained at room temperature for 18-22h. The reaction mixture was diluted with EtOH, concentrated in vacuo and dried to give a residue which was purified by chromatographic column. Yield: 62-95%.

  • 3
  • [ 25084-14-4 ]
  • [ 6973-09-7 ]
  • 5-Nitro-furan-2-carboxylic acid (4-methyl-3-sulfamoyl-phenyl)-amide [ No CAS ]
  • 4
  • [ 696-45-7 ]
  • [ 25084-14-4 ]
  • 5-nitro-furan-2-carboxylic acid (6-methoxy-pyrimidin-4-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With pyridine; In dichloromethane; at 50℃; for 14h; To the mixture of 5-nitro-furan-2-carbonyl chloride (667 mg, 3. 8 MMOL) in CH2CI2 (5 ML) was added 4-amino 6-methoxy pyrimidine (475 mg, 3. 8 MMOL) followed by pyridine (5 ML) and reaction was stirred for 14 hr. at 50°C. The reaction was followed as explained in method 2 to yield 550 mg (40percent) of compound 51. TLC: Rf 0. 53 (1: 1 hexane: ethyl acetate).'HNMR (500 MHz, CDCI3) : No.4. 04 (3H, s), 7.44 (2H, q, J = 4.04, 8. 06 Hz), 7.65 (1 H, d, J = 0.97 Hz), 8.58 (1H, d, J = 0. 98 Hz), 8.85 (1H, s); CNMR (300 MHZ, CDCIG) : 53.77, 95.60, 111.79, 117.34, 145.98, 154.13, 156.21, 170.80 ; EI-Mass : 263 (M+-1) ; IR : 1576,1684, 3123 cm-1.
  • 5
  • [ 25084-14-4 ]
  • [ 5464-79-9 ]
  • 5-nitro-furan-2-carboxylic acid (4-methoxy-benzothiazol-2-yl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With pyridine; In dichloromethane; at 20℃; for 14h; To the mixture of 5-Nitro-furan-2-carbonyl chloride (667 mg, 3. 8 MMOL) in GH2CI2 (5 ml) was added 2-amino 4-methoxy benzothiazole (684 mg, 3. 8 MMOL) followed by pyridine (5 ml) and the reaction mixture was stirred for 14 hr. at room temperature. The reaction was followed as explained in method 2 to yield 480 mg (29%) of compound 50. TLC: Rf 0.37 (1: 1 hexane: ethyl acetate). 1HNMR (500 MHz, CD3OD) : No.4. 03 (3H, s), 7.04 (1 H, d, J = 8. 06 Hz), 7.30 (1 H, t, J = 8. 06 Hz), 7.44 (1H, d, J = 8.06 Hz), 7.53 (1H, m), 7.59 (1H, d, J = 3.66 Hz); 13CNMR (300 MHz, CDCI3) : 29. 15, 55.36, 106.56, 111.59, 113.07, 117.70, 125.12 ; Ei-Mass : 318 (M+-1) ; IR : 1561,1701 cm-1.
480 mg (29%) With pyridine; In dichloromethane; 5-nitro-furan-2-carboxylic acid(4-methoxy-benzothiazol-2-yl)-amide (50). To the mixture of 5-Nitro-furan-2-carbonyl chloride (667 mg, 3.8 mmol) in CH2Cl2 (5 ml) was added 2-amino 4-methoxy benzothiazole (684 mg, 3.8 mmol) followed by pyridine (5 ml) and the reaction mixture was stirred for 14 hr. at room temperature. The reaction was followed as explained in method 2 to yield 480 mg (29%) of compound 50. TLC: Rf 0.37 (1:1 hexane:ethyl acetate). 1H-NMR (500 MHz, CD3OD): delta4.03 (3H, s), 7.04 (1H, d, J=8.06 Hz), 7.30 (1H, t, J=8.06 Hz), 7.44 (1H, d, J=8.06 Hz), 7.53 (1H, m), 7.59 (1H, d, J=3.66 Hz); 13C-NMR (300 MHz, CDCl3): 29.15, 55.36, 106.56, 111.59, 113.07, 117.70, 125.12; EI-Mass: 318 (M+-1); IR: 1561,1701 cm-1.
  • 6
  • [ 25084-14-4 ]
  • [ 4393-09-3 ]
  • 5-nitro-furan-2-carboxylic acid 2,3-dimethoxy-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With triethylamine; In dichloromethane; at 20℃; for 14h; To the mixture of 5-nitro-furan-2-carbonyl chloride (877 mg, 5 MMOL) in CH2CI2 (10 ml) was added to <strong>[4393-09-3]2,3-dimethoxy benzyl amine</strong> (0.734 ML, 5 MMOL) in Et3N (3 ML) and reaction was stirred for 14 hr. at room temperature. The reaction was followed as explained in method 2 to yield 830 mg (54%) of compound 53. Rf 0. 48 (1: 1 hexane: ethyl ACETATE). 1HNMR (500 MHz, CDCIS) : E53. 90 (3H, s), 3.95 (3H, s) 4.65 (2H, d, J = 6. 10 Hz), 6.92 (2H, dd, J = 1. 46,7. 05 HZ), 6.95 (1 H, dd, J = 1.46, 7. 81 Hz), 7.03-7. 09 (3H, m) ; 13CNMR (300 MHz, CDC13) : 38.91, 55.21, 60.19, 111. 88, 115.27, 120. 84, 123.63, 130.04, 146.76, 147.66, 152.11, 155.54 ; EL-MASS : 329 (M++23), 305 (M+-1) ; IR : 1671,3323 cm-1.
830 mg (54%) In dichloromethane; triethylamine; 5-nitro-furan-2-carboxylic acid 2,3-dimethoxy-benzylamide (53). To the mixture of 5-nitro-furan-2-carbonyl chloride (877 mg, 5 mmol) in CH2Cl2(10 ml) was added to <strong>[4393-09-3]2,3-dimethoxy benzyl amine</strong> (0.734 ml, 5 mmol) in Et3N (3 ml) and reaction was stirred for 14 hr. at room temperature. The reaction was followed as explained in method 2 to yield 830 mg (54%) of compound 53. Rf 0.48 (1:1 hexane:ethyl acetate). 1H-NMR (500 MHz, CDCl3): delta3.90 (3H, s), 3.95 (3H, s) 4.65 (2H, d, J=6.10 Hz), 6.92 (2H, dd, J=1.46, 7.05 Hz), 6.95 (1H, dd, J=1.46, 7.81 Hz), 7.03-7.09 (3H, m); 13C-NMR (300 MHz, CDCl3): 38.91, 55.21, 60.19, 111.88, 115.27, 120.84, 123.63, 130.04, 146.76, 147.66, 152.11, 155.54; EI-Mass: 329 (M++23), 305 (M+-1); IR: 1671, 3323 cm-1.
  • 7
  • [ 216144-45-5 ]
  • [ 25084-14-4 ]
  • 5-nitro-furan-2-carboxylic acid 4-(4-methyl-piperazin-1-yl)-benzylamide [ No CAS ]
  • 8
  • [ 581812-68-2 ]
  • [ 25084-14-4 ]
  • [ 831203-75-9 ]
YieldReaction ConditionsOperation in experiment
1.96 g With triethylamine In tetrahydrofuran at 20℃; for 12h;
  • 9
  • [ 214759-74-7 ]
  • [ 25084-14-4 ]
  • 5-nitro-furan-2-carboxylic acid 4-morpholin-4-yl-benzylamide [ No CAS ]
  • 10
  • [ 25084-14-4 ]
  • [ 19293-58-4 ]
  • 5-nitro-furan-2-carboxylic acid 4-dimethylamino-benzylamide [ No CAS ]
  • 11
  • [ 25084-14-4 ]
  • [ 148546-99-0 ]
  • 5-nitro-furan-2-carboxylic acid [3-(4-methyl-piperazin-1-yl)-phenyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In dichloromethane; triethylamine; 5-Nitro-furan-2-carboxylic acid [3-(4-methyl-piperazin-1-yl)-phenyl]-amide (60). 5-Nitro-furan-2-carbonyl chloride (438 mg, 2.5 mmol) in CH2Cl2 (10 mL) was added to a mixture of amine 37b (382 mg, 2.0 mmol) in Et3N (1.04 mL, 7.5 mmol) and the mixture was stirred for 12 hrs at room temperature. Reaction was carried out as explained above to afford 593 mg of amide 60 in 90% yields. 1H-NMR (500 MHz, CDCl3): delta 2.38 (3Hs, s), 2.60 (4Hs, t, J=4.64 Hz), 3.28 (4Hs, t, J=4.51 Hz), 6.8 (1H, d, J=8.3 Hz), 7.08 (1H, d, J=8.05 Hz), 7.25-7.32 (2Hs, m), 7.37-7.45 (2Hs, m), 7.48 (1H, dd, J=1.22, 3.66 Hz), 8.17 (1H, bs); 13C-NMR (300 MHz, CD3OD): ppm 44.16, 47.92, 53.98, 107.99, 111.48, 111.70, 112.26, 115.49, 128.50, 137.57, 147.55, 151.16, 154.73; ESI-MASS: 331.3 (M+1). Anal. Calcd. for C16H18N4O4: C, 58.17; H, 5.49; N, 16.96. Found: C, 57.94; H, 5.40; N, 16.92.
  • 12
  • [ 25084-14-4 ]
  • [ 159724-40-0 ]
  • 5-nitro-furan-2-carboxylic acid (3-morpholin-4-yl-phenyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In dichloromethane; triethylamine; 5-Nitro-furan-2-carboxylic acid(3-morpholin-4-yl-phenyl)-amide (59). 5-Nitro-furan-2-carbonyl chloride (438 mg, 2.5 mmol) in CH2Cl2 (10 mL) was added to a mixture of amine 36b (356 mg, 2.0 mmol) in Et3N (1.04 mL, 7.5 mmol) and the mixture was stirred for 12 hrs at room temperature. Reaction was carried out as explained above to afford 494 mg of amide 59 in 78% yields. 1H-NMR (500 MHz, CDCl3): delta 3.23 (4Hs, t, J=4.63 Hz), 3.89 (4Hs, t, J=4.88 Hz), 6.77 (1H, dd, J=2.19, 8.3 Hz), 7.1 (1H, dd, J=1.46, 7.81 Hz), 7.30 (1H, t, J=8.05 Hz), 7.38 (1H, d, J=3.66 Hz), 7.46-7.5 (2Hs, m), 8.20 (1H, bs); 13C-NMR (300 MHz, CDCl3): ppm 51.75, 69.37, 110.78, 114.99, 115.26, 115.31, 119.17, 132.16, 140.47, 150.80, 154.44, 157.39; ESI-MASS: 318.3 (M+1).
  • 13
  • [ 852180-47-3 ]
  • [ 25084-14-4 ]
  • [ 831203-79-3 ]
  • 14
  • [ 25084-14-4 ]
  • [ 10282-31-2 ]
  • 5-nitro-furan-2-carboxylic acid 4-morpholin-4-yl-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% In dichloromethane; triethylamine Scheme 2 5-Nitro-furan-2-carboxylic acid 4-morpholin-4-yl-benzylamide (64). 5-Nitro-furan-2-carbonyl chloride (438 mg, 2.5 mmol) in CH2Cl2 (10 mL) was added to a mixture of crude amine 44b (384 mg, 2.0 mmol) in Et3N (1.04 mL, 7.5 mmol) and the mixture was stirred for 12 hrs at room temperature. Reaction was carried out as explained above to afford 469 mg of amide 64 in 71% yields. 1H-NMR (500 MHz, CDCl3): δ 3.22 (4Hs, t, J=4.88 Hz), 3.92 (4Hs, t, J=4.88 Hz), 4.61 (2Hs, d, J=5.61 Hz), 6.78-6.82 (1H, bs), 6.96 (2Hs, d, J=8.78 Hz), 7.31-7.35 (3Hs,. m), 7.41 (1H, d, J=3.90 Hz); 13C-NMR (300 MHz, DMSO-D6): ppm 41.81, 48.56, 65.99, 113.34, 114.99, 115.42, 128.39, 129.20, 148.29, 150.23, 151.37, 155.88; ESI-MASS: 332.4 (M+1); Anal. Calcd. for C16H17N3O5: C, 58.00; H, 5.17; N, 12.68. Found: C, 57.71;H, 5.23;N, 12.41.
  • 15
  • [ 25084-14-4 ]
  • [ 34334-28-6 ]
  • 5-nitro-furan-2-carboxylic acid 4-(4-methyl-piperazin-1-yl)-benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In dichloromethane; triethylamine; 5-Nitro-furan-2-carboxylic acid 4-(4-methyl -piperazin-1-yl)-benzylamide (65). 5-Nitro-furan-2-carbonyl chloride (438 mg, 2.5 mmol) in CH2Cl2 (10 mL) was added to a mixture of crude amine 45b (410 mg, 2.0 mmol.) in Et3N (1.04 mL, 7.5 mmol) and the mixture was stirred for 12 hrs at room temperature. Reaction was carried out as explained above to afford 481 mg of amide 65 in 70% yields. 1H-NMR (500 MHz, CDCl3): delta 2.41 (3Hs, s), 2.63 (4Hs, t, J=4.88 Hz), 3.27 (4Hs, t, J=4.88 Hz), 4.6 (2Hs, d, J=5.61 Hz), 6.78-6.83 (1H, bs), 6.97 (2Hs, d, J=8.78 Hz), 7.31 (2Hs, d, J=8.78 Hz), 7.33 (1H, d, J=3.90 Hz), 7.41 (1H, d, J=3.90 Hz); 13C-NMR (300 MHz, CDCl3): ppm 41.71, 44.02, 48.06, 53.94, 111.31, 114.88, 115.52, 127.89, 128.91, 147.54, 149.95, 156.61; ESI-MASS: 345.3 (M+1); Anal. Calcd. for C17H2ON4O4: C, 59.29; H, 5.85; N, 16.27. Found: C, 59.16; H, 5.91; N, 16.19.
  • 16
  • [ 25084-14-4 ]
  • [ 51135-96-7 ]
  • (4-Benzyl-4-hydroxy-piperidin-1-yl)-(5-nitro-furan-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
480 mg (45%) In dichloromethane; triethylamine 5 Scheme 3 (4-Benzyl-4-hydroxy-piperidin-1-yl)-(5-nitro-furan-2-yl)-methanone (79). 5-Nitro-furan-2-carbonyl chloride (558 mg, 3.18 mmol) in CH2Cl2 (10 mL) was added to 4-benzyl-4-hydroxy piperidine (607 mg, 3.18 mmol) in Et3N (3 mL). The reaction mixture was stirred for 14 hrs at room temperature. The reaction was followed as explained above to yield 480 mg (45%) of compound 79; TLC: Rf 0.60 (ethyl acetate); 1H-NMR (500 MHz, DMSO): δ 1.4-1.6 (4H, m), 2.72 (2H, s), 3.05-3.2 (1H, bs), 3.46(1H, t, J=11.72 Hz), 3.87 (1H, d, J=11.71 Hz), 4.14 (1H, d, J=11.47 Hz), 4.58 (1H, s), 7.17-7.24 (4H, m), 7.74 (1H, d, J=3.91 Hz); 13C-NMR (300 MHz, DMSO): 35.7, 36.69, 42.57, 48.27, 68.36, 112.77, 116.33, 125.84, 127.54, 130.5, 137.31, 148,151, 156.44; ESI-Mass: 353.1 (M+23); Anal. Calcd for C17H18N2O5: C, 61.81; H, 5.49; N, 8.48. Found: C, 61.68; H, 5.43; N, 8.45.
  • 17
  • [ 25084-14-4 ]
  • [ 51639-48-6 ]
  • 1-{4-[4-(5-Nitro-furan-2-carbonyl)-piperazin-1-yl]-phenyl}-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
540 mg (55%) In dichloromethane; triethylamine; 1-{4-[4-(5-Nitro-furan-2-carbonyl)-piperazin-1-yl]-phenyl}-ethanone (91). 5-Nitro-furan-2-carbonyl chloride (558 mg, 3.18 mmol) in CH2Cl2 (10 mL) was added to 4-piperazino acetophenone (649 mg, 3.18 mmol) in Et3N (3 mL). The reaction mixture was stirred for 14 hrs at room temperature. The reaction was followed as explained above to yield 540 mg (55%) of compound 91; TLC: Rf 0.68 (ethyl acetate); 1H-NMR (500 MHz, DMSO) delta 2.24 (3H, s), 3.49 (4H, t, J=4.88 Hz), 3.72-3.96 (4H, 2bs), 7.0 (2H, d, J=9.03 Hz), 7.34 (1H, d, J=3.9 Hz), 7.8 (1H, d, J=3.9 Hz), 7.84 (2H, d, J=8.78 Hz); 13C-NMR (300 MHz, DMSO): 26.0, 41.84, 46.3, 112.78, 113.12, 117.22, 126.91, 130.02, 147.47, 151.18, 153.16, 156.69; ESI-Mass: 344 (M+1); Anal. Calcd for C17H17N3O5: C, 59.47; H, 4.99; N, 12.24. Found: C, 59.19; H, 5.08; N, 11.98.
  • 18
  • [ 252758-94-4 ]
  • [ 25084-14-4 ]
  • 5-nitro-furan-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-phenyl]-amide [ No CAS ]
  • 19
  • [ 25084-14-4 ]
  • [ 180605-36-1 ]
  • 5-nitro-furan-2-carboxylic acid [2-(4-methyl-piperazin-1-yl)-phenyl]-amide [ No CAS ]
  • 20
  • [ 402924-76-9 ]
  • [ 25084-14-4 ]
  • 5-nitro-furan-2-carboxylic acid [2-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With PS-morpholine In 1,4-dioxane at 70℃; for 2h;
  • 21
  • [ 25084-14-4 ]
  • [ 154590-66-6 ]
  • C21H22FN5O7 [ No CAS ]
  • 22
  • [ 25084-14-4 ]
  • [ 7417-18-7 ]
  • [ 1419943-05-7 ]
  • 23
  • [ 25084-14-4 ]
  • [ 35364-79-5 ]
  • [ 1419943-28-4 ]
  • 24
  • [ 25084-14-4 ]
  • [ 349-55-3 ]
  • [ 672884-92-3 ]
  • 25
  • [ 25084-14-4 ]
  • [ 393-15-7 ]
  • [ 1418733-83-1 ]
  • 26
  • [ 25084-14-4 ]
  • [ 2835-96-3 ]
  • [ 1418733-84-2 ]
  • 27
  • [ 25084-14-4 ]
  • [ 19156-63-9 ]
  • [ 908557-52-8 ]
YieldReaction ConditionsOperation in experiment
420 mg With triethylamine In dichloromethane at 20℃; for 5h;
  • 28
  • [ 25084-14-4 ]
  • [ 31891-06-2 ]
  • [ 908502-60-3 ]
  • 29
  • [ 25084-14-4 ]
  • [ 1001020-08-1 ]
  • [ 1580443-27-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: To the stirred solution of compound IV (1.00equiv), in dichloromethane at 0C, was added DIPEA (2.50equiv) stirred for few minutes then added compound V (1.20equiv) drop wise under N2 atm at same temperature, and allowed to stir the reaction mixture at rt for 6h. the reaction mixture was diluted with DCM and washed with H2O, the separated organic layer was dried over anhy Na2SO4 and evaporated under vacuo, the obtained product was purified by column chromatography using EtOAc/Hexanes as eluent.
  • 32
  • [ 25084-14-4 ]
  • [ 93-05-0 ]
  • N-(4-(diethylamino)phenyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.7% With sodium hydroxide In water at 3 - 20℃; for 3h; 1-1 1-1,Synthesis of N-(4-(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide Water (40 mL), NaOH (1.13 g, 28.25 mmol),4-(Diethylamino)phenylamine (Compound 2) (2.34 g, 14.13 mmol) was added to a 100 mL reaction flask and stirred at room temperature until dissolved.After cooling to 3 to 5 ° C in an ice bath, 5-nitrofuran-2-carbonyl chloride (compound 1) was added in portions.(2.00g, 11.39mmol), after the addition, continue to stir for 1 hour.It was then stirred at room temperature for 2 hours to give a pale yellow-green solution.The above solution was poured into a mixture consisting of 37% concentrated hydrochloric acid (54.3 mL) and ice (about 20.0 g), crystals were precipitated, suction filtered, and the filter cake was washed with water and acetone, respectively.Light yellow solid after dryingN-(4-(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide (Compound 3),2.89 g, yield 83.7%.
83.7% Stage #1: N,N-diethylaniline With sodium hydroxide In water Stage #2: 5-nitrofuran-2-carboxylic chloride at 3 - 20℃; for 3h; 1-1 Example 1: N- (4- (diethylamino) phenyl) -5 - ((4-neopentyl-phenyl) diazenyl) furan-2-carboxamido 1-1, Synthesis of N-(4-(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide Add water (40 mL), NaOH (1.13 g, 28.25 mmol), 4-(diethylamino)phenylamine (Compound 2) (2.34 g,14.13mmol) to a 100 mL reaction flask and stir at room temperature until Dissolved.After cooling to 3 to 5 ° C in an ice bath,5-nitrofuran-2-carbonyl chloride (Compound 1) (2.00 g, 11.39 mmol) was added portionwise, and after the addition, stirring was continued for 1 hour, thenstirredatroom temperature. After 2 hours, a pale yellow-green solution was obtained.The above solution was poured into a mixture consisting of 37% concentrated hydrochloric acid (54.3 mL) and ice (about20.0 g), crystals were precipitated, suction filtered, and the filter cake was washed with water and acetone, and dried to give a pale yellow solid N-(4 -(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide (Compound 3), 2.89 g, yield 83.7%.
83.7% With sodium hydroxide In water at 3 - 20℃; for 3h; 1.1 Example 1: Synthesis of N-(4-(diethylamino)phenyl)-5-((pyridyl-4)diazenyl)furan-2-carboxamide 1-1Synthesis of N-(4-(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide Water (40 mL), NaOH (1.13 g, 28.25 mmol),4-(Diethylamino)phenylamine (Compound 2) (2.34 g, 14.13 mmol) was added to a 100 mL reaction flask and stirred at room temperature until dissolved. After cooling to 3 to 5 ° C in an ice bath, 5-nitrofuran-2-carbonyl chloride (Compound 1) (2.00 g, 11.39 mmol) was added portionwise. After the addition, stirring was continued for 1 hour, then stirred at room temperature 2 In hours, a pale yellow-green solution was obtained. The above solution was poured into a mixture consisting of 37% concentrated hydrochloric acid (54.3 mL) and ice (about 20.0 g), crystals were precipitated, suction filtered, and the filter cake was washed with water and acetone, and dried to give a pale yellow solid N-(4) -(Diethylamino)phenyl)-5-nitrofuran-2-carboxamide (Compound 3), 2.89 g, yield 83.7%.
  • 33
  • [ 25084-14-4 ]
  • [ 17797-11-4 ]
  • C14H13ClN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Synthesis of 21 General procedure: Step B The crude from above (0.16 g, 0.97 mmol) was dissolved in dry DCM (5 mL) and a solution of 5-nitro-2-furoyl chloride (0.17 g, 0.97 mmol) in dry DCM (5 mL) was added dropwise, followed by dropwise addition of Et3N (0.27 mL, 1.9 mmol) at room temperature. The crude reaction was stirred at room temperature until reaction completion, diluted with DCM (10 mL), and washed with saturated aqueous brine solution (15 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 34
  • [ 25084-14-4 ]
  • [ 306761-54-6 ]
  • 5-nitro-N-(2-(4-(trifluoromethyl)phenyl)propan-2-yl)furan-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃;Inert atmosphere; General procedure: Step B The crude from above (0.16 g, 0.97 mmol) was dissolved in dry DCM (5 mL) and a solution of 5-nitro-2-furoyl chloride (0.17 g, 0.97 mmol) in dry DCM (5 mL) was added dropwise, followed by dropwise addition of Et3N (0.27 mL, 1.9 mmol) at room temperature. The crude reaction was stirred at room temperature until reaction completion, diluted with DCM (10 mL), and washed with saturated aqueous brine solution (15 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 35
  • [ 25084-14-4 ]
  • [ 18655-50-0 ]
  • N-(3-(4-chlorophenyl)propyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To a stirred solution of 5-nitro-2-furoyl chloride (0.10 g, 0.57 mmol) in dry DCM (5 mL) at 0 C was added a solution of benzylamine (0.060 mL, 0.57 mmol) in dry DCM dropwise, followed by addition of Et3N (0.10 mL, 0.68 mmol). After that, the solution was stirred at room temperature until reaction completion. Crude reaction was diluted with DCM (10 mL) and washed with saturated aqueous brine solution (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 36
  • [ 25084-14-4 ]
  • [ 30568-44-6 ]
  • N-(2-(4-methoxyphenyl)propan-2-yl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 20℃; Inert atmosphere; Synthesis of 21 Step B The crude from above (0.16 g, 0.97 mmol) was dissolved in dry DCM (5 mL) and a solution of 5-nitro-2-furoyl chloride (0.17 g, 0.97 mmol) in dry DCM (5 mL) was added dropwise, followed by dropwise addition of Et3N (0.27 mL, 1.9 mmol) at room temperature. The crude reaction was stirred at room temperature until reaction completion, diluted with DCM (10 mL), and washed with saturated aqueous brine solution (15 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 37
  • [ 25084-14-4 ]
  • [ 41049-53-0 ]
  • 5-nitro-N-(1-phenylcyclopropyl)furan-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Synthesis of JSF-3449 General procedure: To a stirred solution of 5-nitro-2-furoyl chloride (0.10 g, 0.57 mmol) in dry DCM (5 mL) at 0 °C was added a solution of benzylamine (0.060 mL, 0.57 mmol) in dry DCM dropwise, followed by addition of Et3N (0.10 mL, 0.68 mmol). After that, the solution was stirred at room temperature until reaction completion. Crude reaction was diluted with DCM (10 mL) and washed with saturated aqueous brine solution (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 38
  • [ 25084-14-4 ]
  • [ 61501-04-0 ]
  • N-(2,2-dimethyl-1-phenylpropyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To a stirred solution of 5-nitro-2-furoyl chloride (0.10 g, 0.57 mmol) in dry DCM (5 mL) at 0 C was added a solution of benzylamine (0.060 mL, 0.57 mmol) in dry DCM dropwise, followed by addition of Et3N (0.10 mL, 0.68 mmol). After that, the solution was stirred at room temperature until reaction completion. Crude reaction was diluted with DCM (10 mL) and washed with saturated aqueous brine solution (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 39
  • [ 91271-84-0 ]
  • [ 25084-14-4 ]
  • N-(4-(morpholinomethyl)benzyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃;Inert atmosphere; General procedure: To a stirred solution of 5-nitro-2-furoyl chloride (0.10 g, 0.57 mmol) in dry DCM (5 mL) at 0 C was added a solution of benzylamine (0.060 mL, 0.57 mmol) in dry DCM dropwise, followed by addition of Et3N (0.10 mL, 0.68 mmol). After that, the solution was stirred at room temperature until reaction completion. Crude reaction was diluted with DCM (10 mL) and washed with saturated aqueous brine solution (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 40
  • [ 25084-14-4 ]
  • [ 90299-04-0 ]
  • N-(2-(naphthalen-2-yl)propan-2-yl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Synthesis of JSF-3449 General procedure: To a stirred solution of 5-nitro-2-furoyl chloride (0.10 g, 0.57 mmol) in dry DCM (5 mL) at 0 °C was added a solution of benzylamine (0.060 mL, 0.57 mmol) in dry DCM dropwise, followed by addition of Et3N (0.10 mL, 0.68 mmol). After that, the solution was stirred at room temperature until reaction completion. Crude reaction was diluted with DCM (10 mL) and washed with saturated aqueous brine solution (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. Product was purified by column chromatography (95% DCM: 5% MeOH).
  • 41
  • [ 25084-14-4 ]
  • [ 7149-10-2 ]
  • N-(4-hydroxy-3-methoxybenzyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: vanillylamine hydrochloride With sodium hydrogencarbonate In chloroform; water at 20℃; for 0.75h; Stage #2: 5-nitrofuran-2-carboxylic chloride In chloroform; water for 0.5h; 5.2.1. General procedure for synthesis of compounds 1-3 General procedure: To a solution of vanillylamine hydrochloride (1.90 g, 10.0 mmol)in water (30 mL), NaHCO3 (2.52 g, 30.0 mmol) was added. Themixture was stirred for 30 min at room temperature and thenchloroform (30 mL) was added. After stirring for 15 min, a solutionof acyl chloride (10.0 mmol) in chloroform (20 mL) was addeddropwise. The mixture was stirred for 30 min and monitored forcompletion by TLC. The organic layer was separated, and the waterlayer was extracted with chloroform (3 20 mL). The organicphases were combined and dried by anhydrous sodium sulfate. Thesolvent was removed under reduced pressure and the residue wasrecrystallized (when needed) to yield the product.
  • 42
  • [ 25084-14-4 ]
  • [ 33322-60-0 ]
  • N-(3-(dimethylcarbamoyl)phenyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% General procedure: Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0C in an ice water bath.Slowly add oxalyl chloride (190 mg, 0.13 mL, 1.5 mmol) dropwise, and then stir at room temperature for 2 hours.The reaction solution is concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a),Without purification, tetrahydrofuran (1 mL) was added for use.Dissolve p-acetaminoaniline (3-3a, 150mg, 1mmol) in tetrahydrofuran (5mL),After adding triethylamine (152mg, 1.5mmol), the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath.After dripping, it was reacted at room temperature until TLC (CH2Cl2:MeOH=15:1) showed that the reaction was complete.Add 30 mL of water to the reaction system, continue to stir for 10 minutes, and then filter with suction.The filter cake was washed successively with 5% hydrochloric acid and 10 mL of distilled water, and a yellow solid was obtained after drying.The yield is 80%, and the melting point is 301-303C (literature value [93] 293C (decomposition)).
  • 43
  • [ 25084-14-4 ]
  • [ 77201-15-1 ]
  • N-(3-(cyclohexylcarbamoyl)phenyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 5-nitrofuran-2-carboxylic chloride With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: 3-amino-benzoic acid cyclohexylamide With triethylamine In tetrahydrofuran at 20℃; Cooling with ice; 58 Example 1 N-(4-Acetylaminophenyl)-4-nitrobenzamide General procedure: Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0°C in an ice water bath.Slowly add oxalyl chloride (190 mg, 0.13 mL, 1.5 mmol) dropwise, and then stir at room temperature for 2 hours.The reaction solution is concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a),Without purification, tetrahydrofuran (1 mL) was added for use.Dissolve p-acetaminoaniline (3-3a, 150mg, 1mmol) in tetrahydrofuran (5mL),After adding triethylamine (152mg, 1.5mmol), the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath.After dripping, it was reacted at room temperature until TLC (CH2Cl2:MeOH=15:1) showed that the reaction was complete.Add 30 mL of water to the reaction system, continue to stir for 10 minutes, and then filter with suction.The filter cake was washed successively with 5% hydrochloric acid and 10 mL of distilled water, and a yellow solid was obtained after drying.The yield is 80%, and the melting point is 301-303°C (literature value [93] 293°C (decomposition)).
  • 44
  • [ 25084-14-4 ]
  • [ 54977-91-2 ]
  • N-(3-(benzylcarbamoyl)phenyl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: 5-nitrofuran-2-carboxylic chloride With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: 3-amino-N-benzylbenzamide With triethylamine In tetrahydrofuran at 20℃; Cooling with ice; 59 Example 1 N-(4-Acetylaminophenyl)-4-nitrobenzamide General procedure: Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0°C in an ice water bath.Slowly add oxalyl chloride (190 mg, 0.13 mL, 1.5 mmol) dropwise, and then stir at room temperature for 2 hours.The reaction solution is concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a),Without purification, tetrahydrofuran (1 mL) was added for use.Dissolve p-acetaminoaniline (3-3a, 150mg, 1mmol) in tetrahydrofuran (5mL),After adding triethylamine (152mg, 1.5mmol), the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath.After dripping, it was reacted at room temperature until TLC (CH2Cl2:MeOH=15:1) showed that the reaction was complete.Add 30 mL of water to the reaction system, continue to stir for 10 minutes, and then filter with suction.The filter cake was washed successively with 5% hydrochloric acid and 10 mL of distilled water, and a yellow solid was obtained after drying.The yield is 80%, and the melting point is 301-303°C (literature value [93] 293°C (decomposition)).
  • 45
  • [ 25084-14-4 ]
  • [ 41616-02-8 ]
  • N1,N3-dimethyl-5-(5-nitrofuran-2-carboxamido)isophthalamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 5-nitrofuran-2-carboxylic chloride With triethylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2h; Stage #2: 3,5-di(methylcarbamoyl)-aniline With triethylamine In tetrahydrofuran at 20℃; Cooling with ice; 68 Example 1 N-(4-Acetylaminophenyl)-4-nitrobenzamide General procedure: Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0°C in an ice water bath.Slowly add oxalyl chloride (190 mg, 0.13 mL, 1.5 mmol) dropwise, and then stir at room temperature for 2 hours.The reaction solution is concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a),Without purification, tetrahydrofuran (1 mL) was added for use.Dissolve p-acetaminoaniline (3-3a, 150mg, 1mmol) in tetrahydrofuran (5mL),After adding triethylamine (152mg, 1.5mmol), the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath.After dripping, it was reacted at room temperature until TLC (CH2Cl2:MeOH=15:1) showed that the reaction was complete.Add 30 mL of water to the reaction system, continue to stir for 10 minutes, and then filter with suction.The filter cake was washed successively with 5% hydrochloric acid and 10 mL of distilled water, and a yellow solid was obtained after drying.The yield is 80%, and the melting point is 301-303°C (literature value [93] 293°C (decomposition)).
  • 46
  • [ 580-15-4 ]
  • [ 25084-14-4 ]
  • N-(quinolin-6-yl)-5-nitrofuran-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% General procedure: Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0C in an ice water bath.Slowly add oxalyl chloride (190 mg, 0.13 mL, 1.5 mmol) dropwise, and then stir at room temperature for 2 hours.The reaction solution is concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a),Without purification, tetrahydrofuran (1 mL) was added for use.Dissolve p-acetaminoaniline (3-3a, 150mg, 1mmol) in tetrahydrofuran (5mL),After adding triethylamine (152mg, 1.5mmol), the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath.After dripping, it was reacted at room temperature until TLC (CH2Cl2:MeOH=15:1) showed that the reaction was complete.Add 30 mL of water to the reaction system, continue to stir for 10 minutes, and then filter with suction.The filter cake was washed successively with 5% hydrochloric acid and 10 mL of distilled water, and a yellow solid was obtained after drying.The yield is 80%, and the melting point is 301-303C (literature value [93] 293C (decomposition)).
Same Skeleton Products
Historical Records