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Chemical Structure| 651-06-9 Chemical Structure| 651-06-9
Chemical Structure| 651-06-9

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Sulfameter a long-acting sulfonamide antibiotic used as a leprostatic agent and to treat urinary tract infections, which blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase as a competitive inhibitors of bacterial para-aminobenzoic acid.

Synonyms: Sulfametoxydiazine; 5-Methoxysulfadiazine; I-2586

4.5 *For Research Use Only !

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Product Details of Sulfameter

CAS No. :651-06-9
Formula : C11H12N4O3S
M.W : 280.30
SMILES Code : O=S(C1=CC=C(N)C=C1)(NC2=NC=C(OC)C=N2)=O
Synonyms :
Sulfametoxydiazine; 5-Methoxysulfadiazine; I-2586
MDL No. :MFCD00006067
InChI Key :GPTONYMQFTZPKC-UHFFFAOYSA-N
Pubchem ID :5326

Safety of Sulfameter

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Sulfameter

* 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 [ 651-06-9 ]

[ 651-06-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 651-06-9 ]
  • [ 16290-93-0 ]
  • [ 63-74-1 ]
  • [ 13418-77-4 ]
  • [ 121-57-3 ]
  • 2
  • [ 651-06-9 ]
  • 4-(5-Methoxy-pyrimidin-2-ylsulfamoyl)-benzenediazonium; chloride [ No CAS ]
  • 3
  • [ 19602-82-5 ]
  • [ 651-06-9 ]
  • C36H30N8O8S4 [ No CAS ]
  • 4
  • [ 699-98-9 ]
  • [ 651-06-9 ]
  • 4-(5,7-dioxo-5,7-dihydro-pyrrolo[3,4-<i>b</i>]pyridin-6-yl)-<i>N</i>-(5-methoxy-pyrimidin-2-yl)-benzenesulfonamide [ No CAS ]
  • 7
  • [ 651-06-9 ]
  • [ 15186-48-8 ]
  • 4-[1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-meth-(E)-ylidene]-amino}-N-(5-methoxy-pyrimidin-2-yl)-benzenesulfonamide [ No CAS ]
  • 8
  • [ 651-06-9 ]
  • [ 5736-03-8 ]
  • 4-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylene]amino}-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide [ No CAS ]
  • 9
  • [ 651-06-9 ]
  • [ 109-77-3 ]
  • 4-(<i>N</i>'-dicyanomethylene-hydrazino)-<i>N</i>-(5-methoxy-pyrimidin-2-yl)-benzenesulfonamide [ No CAS ]
  • 10
  • [ 651-06-9 ]
  • 4-[(3,5-diamino-pyrazol-4-yl)-azo]-N-(5-methoxypyrimidin-2-yl)-benzensulfonamide [ No CAS ]
  • 11
  • [ 651-06-9 ]
  • 4-[3-(benzyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-oxoazetidin-1-yl]-N-(5-methoxypyrimidine-2-yl)benzenesulfonamide [ No CAS ]
  • 12
  • [ 651-06-9 ]
  • 4-{(2R,3S)-3-(benzyloxy)-2-[(1S)-1,2-dihydroxyethyl]-4-oxoazetidin-1-yl}-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide [ No CAS ]
  • 13
  • [ 651-06-9 ]
  • [ 288585-96-6 ]
  • 14
  • [ 651-06-9 ]
  • <i>N</i>-(5-methoxy-pyrimidin-2-yl)-4-(3-oxo-3<i>H</i>-benzo[<i>d</i>]isothiazol-2-yl)-benzenesulfonamide [ No CAS ]
  • 15
  • [ 651-06-9 ]
  • 4-[4-Hydroxy-3-(5-m-tolylamino-[1,3,4]thiadiazol-2-yl)-phenylazo]-N-(5-methoxy-pyrimidin-2-yl)-benzenesulfonamide [ No CAS ]
  • 16
  • [ 651-06-9 ]
  • 4-[4-Hydroxy-3-(5-o-tolylamino-[1,3,4]thiadiazol-2-yl)-phenylazo]-N-(5-methoxy-pyrimidin-2-yl)-benzenesulfonamide [ No CAS ]
  • 17
  • [ 25784-91-2 ]
  • [ 651-06-9 ]
  • [ 372094-80-9 ]
YieldReaction ConditionsOperation in experiment
97% With 2,4-dichlorophenoxyacetic acid dimethylamine; Example 105 N-[4-[(5-Methoxypyrimidin-2-yl)aminosulfonyl]phenyl]-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.377 g, yield 97%) was obtained according to the procedure described in Example 2 using <strong>[651-06-9]sulfameter</strong> (a product of Sigma, 0.280 g, 1.0 mmol), DMA (2.5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.264 g, 1.2 mmol). Rf 0.71 [methylenchloride:methanol=7:1 (v/v)]; 1H-NMR (400 MHz, DMSO-d6, TMS): delta(ppm) 3.80 (3H, s), 7.87 (2H, d, J=8.8 Hz), 7.91 (1H, d, J=8.8 Hz), 7.98 (2H, d, J=8.8 Hz), 8.30 (2H, s), 8.36 (1H, dd, J=2.2, 8.8 Hz), 8.52 (1H, d, J=2.2 Hz), 11.09 (1H, s), 11.46 (1H, br); MS(FAB) m/z: 464 (M+H)+.
  • 18
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • [ 651-06-9 ]
  • [Cu2(4-amino-N-(5-methoxy-2-pyrimidinyl)benzenesulfonamide(-H))4]3*2.5H2O [ No CAS ]
  • 19
  • [ 85-44-9 ]
  • [ 651-06-9 ]
  • 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide [ No CAS ]
  • 20
  • [ 117-80-6 ]
  • [ 651-06-9 ]
  • [ 1204290-29-8 ]
  • 21
  • [ 58-27-5 ]
  • [ 651-06-9 ]
  • [ 63875-62-7 ]
  • 22
  • [ 55882-65-0 ]
  • [ 651-06-9 ]
  • N1-feruloylsulphamethoxydiazine [ No CAS ]
  • 23
  • [ 55882-65-0 ]
  • [ 651-06-9 ]
  • C23H22N4O7S [ No CAS ]
  • 24
  • [ 79-04-9 ]
  • [ 651-06-9 ]
  • [ 3363-41-5 ]
  • 25
  • [ 6484-25-9 ]
  • [ 651-06-9 ]
  • N-(5-methoxypyrimidin-2-yl)-4-(2-phenylquinazolin-4-ylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In N,N-dimethyl-formamide; for 22h;Reflux; General procedure: A mixture of 4-chloro-2-phenylquinazoline (1, 2.42 g, 0.01 mol) and sulfonamides (0.012 mol) in dry dimethylformamide (10 mL) was refluxed for 22 h., then left to cool. The solid product formed upon pouring onto ice/water was collected by filtration and recrystallized from ethanol-dimethylformamide to give 2-18, respectively.
  • 26
  • [ 33987-02-9 ]
  • [ 651-06-9 ]
  • 4-(benzo[g]quinazolin-4-ylamino)-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; In N,N-dimethyl-formamide; for 24h;Reflux; General procedure: A mixture of 4-chlorobenzo[g]quinazoline 1 (2.15g, 0.01mmol) and sulfonamides (0.012 mmol) in dry DMF (15mL)was refluxed for 24h., then left to cool. The solid productformed upon pouring onto ice/ water was collected by filtrationand recrystallized from ethanol- DMF to give 2-18, respectively.
  • 27
  • [ 28900-10-9 ]
  • [ 651-06-9 ]
  • 4-(3-cyano-6-methylpyridin-2-ylamino)-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With triethylamine; In N,N-dimethyl-formamide; for 18h;Reflux; General procedure: A mixture of 2-chloro-6-methylnicotinonitrile (II)(1.52 g, 0.01 mol) and corresponding sulfonamide derivatives (0.012 mol) in dry dimethylformamide(10 mL) containing 3 drops of trimethylamine was refluxed for 18 h then left to cool. The solid productformed upon pouring onto ice water was collected byfiltration and recrystallized from ethanol-dimethylformamide to give (III-XX), respectively.
  • 28
  • silver nitrate [ No CAS ]
  • [ 651-06-9 ]
  • C11H11N4O3S(1-)*Ag(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With potassium penicillin V; In water; at 20℃; for 1h; Synthesis of the silver(I) complex The silver(I) complex with <strong>[651-06-9]sulfameter</strong> (AgSMTR) was prepared by dropwise addition of an aqueous solution of AgNO3 (87.6 mg, 0.52 mmol) to an aqueous solution containing 0.50 mmol of SMTR (140.9 mg) and KOH (50.7 mg, 0.90 mmol). The final volume was 6 mL. After 1 h of constant stirring at room temperature, and keeping the reaction protected from light, a white solid precipitated. The powder was isolated by filtration, washed thoroughly with cold water and dried in a desiccator with P4O10. Yield 0.156 g (81%). Anal. Calcd. for [Ag(C11H11N4O3S)] (%): C, 34.1; H, 2.86; N, 14.5. Found (%): C, 33.9; H, 2.15; N, 14.1. The complex is slightly soluble in DMSO and DMF. Molar conductivity: 3.4 S cm2 mol-1.
  • 29
  • [ 651-06-9 ]
  • [ 371756-61-5 ]
  • (Z)-N-(5-methoxypyrimidin-2-yl)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In ethanol; for 21h;Reflux; General procedure: 5.1.2.1. General procedure. A mixture of 2 (1.88 g, 0.01 mol) and sulfa-drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 21 h, then left to cool. The solid product formed was collected by filtration and recrystallized from ethanol-dimethylformamide to give 3-20.
  • 30
  • [ 127172-22-9 ]
  • [ 651-06-9 ]
  • Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methoxylpyrimidin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With acetic acid; In ethanol; for 22h;Reflux; General procedure: General ProcedureA mixture of 2 (2.35 g, 0.01 mol) and sulfa drugs (0.012 mol) in absolute ethanol (10 mL) and glacial acetic acid (5 mL) was refluxed for 22h, and subsequently left to cool. The solid product formed was collected by filtration and recrystallized from acetic acid to give compounds 3-19.
  • 31
  • [ 53901-95-4 ]
  • [ 651-06-9 ]
  • 4-hydroxycinnamoyl sulfamethoxydiazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
5 g (0.0305 mol) of p-hydroxycinnamic acid was weighed into a 250 mL round bottom flask,15 mL of acetic anhydride was added,Shake,140 C for 4 hours,The solvent was evaporated on a rotary evaporator,Ethanol recrystallization,The compound was obtained as a white powder.The prepared acetonitrile was placed in a 100 mL round bottom flask,Add S0Cl2 15mL,At 80 C oil bath,Stirring reflux reaction 6h,The solvent was distilled off under reduced pressure,The first product of acetyl cinnamyl chloride,15 mL of THF was added,dilution,Will weigh <strong>[651-06-9]sulfamethoxydiazine</strong>8.55 g (0.0305 mol) was added thereto,Add pyridine 5mL,Ice bath stirring reaction 1.5h after the natural temperature reaction 24h,After the reaction,The solvent was evaporated on a rotary evaporator,A light white solid,Hydrochloric acid (6 mL) was added,60 water bath stirring reflux after 3 hours to stop the reaction,The solvent was distilled off under reduced pressure,After cooling, distilled water (the amount of water added may be 1: 150 in terms of the molar ratio of water to the reactant cinnamic acid derivative)Precipitation,Decompression pumping,Take precipitation,Tetrahydrofuran and methanol (nu / nu = : ) to give the title compound.The pure compound was obtained as a pale yellow powder in a yield of 80%The compound was recrystallized twice with methanol and THF (V / V = 1: 1)To obtain a colorless bulk crystal
  • 32
  • (Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one [ No CAS ]
  • [ 651-06-9 ]
  • (Z)-N-(5-methoxypyrimidin-2-yl)-4-(3-oxo-3-(10H-phenothiazine-2yl)prop-1-enylamino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In ethanol; for 18h;Reflux; General procedure: A mixture of 3 (2.96g, 0.01mol) and sulfa drugs 4 (0.012mol) in absolute ethanol (10mL) and glacial acetic acid (3mL) was refluxed for 18h. The solid product formed was collected by filtration and crystallized from ethanol to give 5-22.
  • 33
  • [ 66-71-7 ]
  • copper(II) nitrate trihydrate [ No CAS ]
  • [ 651-06-9 ]
  • C34H30CuN10O6S2*3H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% General procedure: The three compounds were prepared using the same method. In summary, a methanolic solution of phen or bpy (0.25 mmol dissolved in 3.0 mL) was added to an aqueous solution containing Cu(NO3)2*3H2O(0.25 mmol, 1.0 mL) and kept under stirring for 1 h. Separately, a solution of deprotonated <strong>[651-06-9]sulfameter</strong> or sulfadimethoxine (0.50 mmol, 3.0 mL of water plus 3.0 mL of methanol) was prepared by the addition of ammonium hydroxide to the sulfa suspension until solubilization.Then, the copper-phen or copper-bpy solution was added to the solution containing the deprotonated sulfonamide. The reactions were maintained under stirring at room temperature for 4 h. The green powder obtained was collected by filtration, washed with cold methanol and dried under vacuum. Found (%): C, 48.1; H, 3.94; N,16.4. Calc. for [Cu(C11H11N4O3S)2(C12H8N2)]·3H2O (%): C, 47.7; H,4.24; N, 16.4. Yield: 0.0920 g, 40%. lambdamax (phosphate buffer, pH=7.4,10 mM): 201 nm (epsilon 83,400M-1·cm-1), 232 nm (epsilon 54,400M-1·cm-1),262 nm (epsilon 59,300M-1·cm-1), 292 nm (epsilon 17,600M-1·cm-1) and326 nm (epsilon 5600M-1·cm-1). Green single-crystals suitable for X-raydiffraction measurements were obtained by recrystallization from a 10:1 methanol:water solution.
  • 34
  • [ 1666-13-3 ]
  • [ 651-06-9 ]
  • N-(5-methoxypyrimidin-2-yl)-4-(phenylselanyl)benzene sulfonamide [ No CAS ]
  • 35
  • [ 651-06-9 ]
  • [ 101834-30-4 ]
  • 4-amino-N-(5-methoxypyrimidin-2-yl)-N-(2-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)ethyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 4.5h; General procedure: Add the raw material sulfonamide or its sodium salt (SA),K2CO3 and N, N-dimethylformamide (DMF), stirred in a water bath at 60 C,Sulfonamide or its sodium salt quickly dissolved, and after 30 min the intermediate IM1 was added.TLC monitors the progress of the reaction. After completion of the reaction, water was added and stirred, and a solid precipitated.Extracted twice with dichloromethane (DCM), combined the organic layers, washed with 5 mL of 0.5 N HCl, and washed with a little water.The organic layer was dried over anhydrous MgSO4. Suction filtration and rotary evaporation under reduced pressure to dry yellow slime.Purify by column chromatography (PE / EA = 2/1, v / v). Collect the eluate and evaporate to dryness under reduced pressure. Most of the solution is colorless and transparent mucus. Add DMF to dissolve the mucous quickly. Add water to precipitate a large amount of solid immediately.Suction filtration, the filter cake was washed with a large amount of water, and dried under vacuum to obtain the target molecule TM2.
 

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