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CAS No. : | 31795-44-5 | MDL No. : | MFCD00003231 |
Formula : | C5H3NaO5S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZTJAVDOZUQPVAV-UHFFFAOYSA-M |
M.W : | 198.13 | Pubchem ID : | 3772036 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; silver nitrate; In water; at 20℃; for 0.5h; | A solution of AgNO3 (1.7 g, 10 MMOL) in 5 mL of water was added with stirring to a solution of NAOH (0. 8 g, 20 MMOL) in 5 mL of water. SODIUM, 5-FORMYL-FURAN-2-SULFONATE (8a) (1 g, 5 MMOL) was added in portions to the resulting brown mixture. The reaction mixture was stirred for 0.5 hr. at room temperature, filtered and the residue was washed with 10 mL of hot water. The chilled filtrate was neutralized with con. HCI and the product was used as such in further reactions.'H NMR (300 MHz, D20): C57. 1 (1 H, d, J = 4.5 Hz), 7.22 (1 H, d, J = 4.5 Hz); 13C NMR (300 MHz, CDCl3) : 112.91, 115.34, 149.42, 152.06, 164.69 ; EL-MASS : 190.6 (M+-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With phosphorus pentachloride; In trichlorophosphate; at 0 - 20℃; for 3h; | Representative activation of [FURANSULFONIC] acids: A flask was charged with 5-formyl-2- [FURANSULFONIC] acid sodium salt (595 mg, 3.00 mmol ; Aldrich 18,381-4), which was suspended in [POCL3] (1.25 mL) and cooled by means of an ice bath. To the stirring suspension was added [PC . S] (3.1 [G,] 15.0 [MMOL)] over a period of 15 min while still cooling. The ice bath was removed and the reaction mixture was allowed to warm to rt. and then stirred at ambient temperature for 3h. TLC (EtOAc-hexane) showed the disappearance of polar components Rf 0 and the formation of a new spot Rf 0.53-0. 62 (both visualized by [KMN04] reagent). The crude reaction mixture was transferred directly to a column of silica gel and eluted with an EtOAc-hexane gradient. Appropriate fractions were combined and concentrated to an oil (580 mg, 77%). Purity > 98% (HPLC 215 nm). UV max (PDA) 216 and [258. 1H] NMR (300 MHz, CDCl3) [8] 7.28 (1H, d, J = 3.6 Hz), 6.84 (1H, d, J = 3.6 [HZ),] 6. [71] (1H, s). [13C] NMR (75 MHz, [CDC13)] [8] 156.0, 150.3, 119.5, 111.2, [61. 1.] |
With phosphorus pentachloride; trichlorophosphate; | Example 11 Synthesis of N-Isopropyl-alpha-[2-(N-morpholinosulfonyl)furan-5-yl]nitrone To a mixture of POCl3, (16.0 mL, 171.66 mmol) and <strong>[31795-44-5]5-formyl-2-furansulfonic acid sodium salt</strong> (15.0 g, 75.71 mmol) was added PCl5 (38.0 g, 182.48 mmol) in portions over a 20 min. period with cooling. The mixture was stirred at room temperature for additional 90 min. The solids (primarily NaCl) were removed by filtration and washed with CH2Cl2 (25 mL). Rotary evaporation of the filtrate gave crude 5-dichloromethyl-2-furansulfonyl chloride (16.43 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen;nickel; In water; at 100℃; under 52505.3 Torr; for 24h; | The salt (ca. 20 mmol, available from Aldrich 18,381-4) was dissolved in water (10 mL) and Raney Ni (0.4 equiv as a slurry in water) was added. The mixture was placed in a tall cylindrical flask with a magnetic stirring bar, which was fitted in to the hydrogenation apparatus. Hydrogen was let in to a pressure of approx. 70 bars and the temperature was raised to approx. [100C.] After 24 h, the heating was discontinued and after another 3 h the apparatus was disassembled. The nickel was removed by filtration and the filtrate was evaporated in vacuo. Toluene was added and the evaporation was repeated to remove residual the water from the product. Yield: 5. [37G] (99%), Purity [>99%. 1H] NMR (300 MHz, [D20)] 4.69 (1H, d), 4.80 (1H, d, [J=0.] 2 Hz), 6.55 (1H, dd, [J=0.] 5 Hz and 3.6 Hz), 6.90 (1H, dd, [J=0.] 4 Hz and 3.5 Hz); [13C] NMR (75 MHz, D2O) [No. ] 56.0, 109.2, 112.8, 151.1, 156.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol;Heating / reflux; | To a solution [OF 4-HYDRAZINO-1- (3-CHLORO-PHENYL)-1 H-PYRAZOLO] [3, 4-d] pyrimidine (Intermediates Example S) (50 mg, 0. [17MMOL)] in [ETOH] (3 mL) was added 5-formyl- [FURAN-2-SULFONIC] acid sodium salt (60mg, 0.25 [MMOL).] The reaction mixture was [REFLUXED] overnight. The cooled solution was filtered to collect pure product (69 mg, [92OXO] yield) 'H NMR (400 MHz, DMSO) [812.] 32 (brs, 1H), 8.65 (s, 1H), 8.54 (s, 1H), 8.46 (s, 1H), 8.28 (d, 1H), 8.16 (s, 1H), 7.61 (t, 1H), 7.43 (d, 1H), 6.99 (d, 1H), 6.57 (d, 1H) ppm; ES-MS m/z 419 (MH+), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; triethylamine; In ethanol; water; | Synthesis of thiopyridone III"" 5-Formyl-2-furansulfonic acid, sodium salt (1.90 g., 9.59 mmol) and hydrazine hydrate (2 mL) were dissolved in 20 mL absolute ethanol. The mixture was then heated at reflux for 1 hour. The mixture was concentrated in vacuo and the residue was triturated with diethyl ether. Ethanol is added to give the hydrazone shown as a colorless granular solid of suitable purity for further use. The above hydrazone (3.20 g., 15.2 mmol), pyran-4-thione (1.70 g., 15.2 mmol), and triethylamine (2.19 mL) were dissolved in 40 mL absolute ethanol. The reaction mixture was heated at ~65 C. for 18 hours then was allowed to cool, and the resulting solids were collected by filtration. The crude solid was dissolved in water and chromatographed on C-18 silica gel using water as eluent. The product containing fractions were frozen and lyophilized to provide thiopyridone III"" (2.40 g., 7.84 mmol; 52%). 1H-NMR (300 MHz, DMSO-d6): delta 8.82 (s, 1H, N=CH), 8.11 (d, 2H, J=7 Hz, 2*C=CH), 7.21 (d, 2H, J=7 Hz, 2*C=CH), 7.16 (d, 1H, J=3 Hz, furyl), 6.66 (d, 1H, J=3 Hz, furyl). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; | Example 11 Synthesis of N-Isopropyl-alpha-[2-(N-morpholinosulfonyl)furan-5-yl]nitrone To a mixture of POCl3, (16.0 mL, 171.66 mmol) and <strong>[31795-44-5]5-formyl-2-furansulfonic acid sodium salt</strong> (15.0 g, 75.71 mmol) was added PCd5 (38.0 g, 182.48 mmol) in portions over a 20 min. period with cooling. The mixture was stirred at room temperature for additional 90 min. The solids (primarily NaCl) were removed by filtration and washed with CH2 Cl2 (25 mL). Rotary evaporation of the filtrate gave crude 5-dichloromethyl-2-furansulfonyl chloride (16.43 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium dichromate; sulfuric acid; In water; | Example 7 Synthesis of N-n-Butyl-5-(N-n-butylcarbamoyl)furan-2-sulfonamide A suspension of <strong>[31795-44-5]5-formyl-2-furansulfonic acid sodium salt</strong> (90 g, 0.454 mol) and potassium dichromate (89.1 g, 0.303 mol) in water (350 mL) was heated to reflux. With the heat off, a solution of sulfuric acid (98%, 55 mL) and water (50 mL) was added dropwise for 40 min. The reaction mixture was refluxed for an additional 3 hours and then cooled to room temperature. The pH of the reaction mixture was adjusted to about 10 with potassium hydroxide. After filtration, the filtrate was concentrated to ca. 200 mL. Chromatography of the residue on silica gel using methanol as the eluant gave 43.5 g of crude 5-carboxy-2-furansulfonic acid sodium/potassium salt. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
i) AKtertf-butyl)-5-cyanoftiran-2-sulfonainide; A solution of 5-formylfuran-2-sulfonic acid sodium salt (2.97g), and hydroxylaminehydrochloride (1.05g) in H2O (1.35mL) and acetic acid (21mL) was heated at 60C for 4h.After cooling to room temperature the solvent was removed in vacua. The crude residue wastriturated with Et2O (3 x 50mL) and dried under high vacuum to give a crude pale brownsolid. A solution of this material (3.7g) in phosphorusoxychloride (lOOmL) was heated at60C for 18h. After cooling to room temperature the mixture was partitioned between ice-water (lOOmL) and EtOAc (lOOmL). The aqueous layer was separated and further extractedwithEtOAc (2 x lOOmL). The combined organic phases were washed with brine (lOOmL),dried (MgSCU), filtered and evaporated to dryness in vacua to give a crude brown oil. To asolution of this crude oil (1.6g) in DCM (85mL) was added te/t-butylamine (1.8mL). Afterstirring at room temperature for 2 days the mixture was filtered through celite, washing withDCM (2 x 20mL). The filtrate was evaporated to dryness in vacua. The resulting crudematerial was purified by column chromatography using EtOAc/isohexane (2:8) as eluent togive the subtitle compound as a pale yellow oil. Yield: l.Og.MS: APCI(-ve) 227 [M-H] |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In the preferred embodiments of the present invention the aldehyde with an acidic function is selected from the group consisting of STR5 5-formyl-2-furansulfonic acid sodium salt, STR6 o-benzaldehyde sulfonic acid, STR7 4-methoxybenzaldehyde-3-sulfonic acid, STR8 4-hydroxybenzaldehyde-3-sulfonic acid, STR9 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol; at 0℃; for 0.5h; | General procedure: Sulfanilamide (1.0 equiv) was dissolved in dry MeOH and theappropriate aldehyde (1.0 equiv) was added to the reaction. Thesolution was stirred until the formation of a precipitate was completedwhich was collected by filtration, washed with ice-coldMeOH and dried under vacuo to afford the desired compounds 1-17. |
[ 98027-63-5 ]
5-Sulfamoylfuran-2-carboxylic acid
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