Conditions | Yield |
---|---|
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With calcium carbonate In toluene at 20 - 65℃; Stage #2: With water; sodium hydroxide In toluene at 100 - 115℃; Stage #3: With acetic acid pH=5 - 5.5; Reagent/catalyst; | 98.5% |
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Stage #2: With sodium hydroxide for 2h; Inert atmosphere; Reflux; | 65% |
Stage #1: 2-aminopyrimidine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h; Stage #2: With sodium hydroxide for 2h; Reflux; |
N-benzylidene-sulfanilic acid pyrimidin-2-ylamide
sulfadiazine
Conditions | Yield |
---|---|
With water In acetone at 20℃; for 0.666667h; Irradiation; | 98% |
4-amino-N-(diaminomethylene) benzenesulfonamide
3-ethoxyacrolein
sulfadiazine
Conditions | Yield |
---|---|
In ethanol at 100℃; for 4h; Green chemistry; | 91% |
3-butoxyacrolein
4-amino-N-(diaminomethylene) benzenesulfonamide
sulfadiazine
Conditions | Yield |
---|---|
In butan-1-ol at 100℃; for 4h; Green chemistry; | 90.8% |
Malondialdehyde
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
sulfadiazine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 65℃; for 2h; Temperature; | 89% |
3-methoxyacrolein
4-amino-N-(diaminomethylene) benzenesulfonamide
sulfadiazine
Conditions | Yield |
---|---|
In methanol at 100℃; for 4h; Temperature; Green chemistry; | 87% |
2-aminopyrimidine
3-(4-acetylamino-benzenesulfonyl)-2-benzenesulfonylimino-2,3-dihydro-thiazole
sulfadiazine
Conditions | Yield |
---|---|
und anschliessenden Erhitzen mit wss. NaOH; |
Conditions | Yield |
---|---|
und anschliessenden Erhitzen mit wss. NaOH; |
Conditions | Yield |
---|---|
With potassium carbonate |
Conditions | Yield |
---|---|
With potassium carbonate |
4-nitro-N-pyrimidin-2-ylbenzenesulfonamide
sulfadiazine
Conditions | Yield |
---|---|
With hydrogenchloride; iron | |
With palladium 10% on activated carbon In tetrahydrofuran; methanol; ethyl acetate at 50℃; under 37503.8 Torr; | |
With hydrogenchloride; iron |
Conditions | Yield |
---|---|
With calcium hydroxide | |
With hydrogenchloride | |
With sodium hydroxide | |
With sodium hydroxide In methanol; 1,2-dimethoxyethane at 120℃; for 16h; | |
With sodium hydroxide |
sulfadiazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: aq. NaOH solution View Scheme | |
Multi-step reaction with 2 steps 1: pyridine / acetonitrile / 3.08 h / 60 °C 2: sodium hydroxide / methanol; 1,2-dimethoxyethane / 16 h / 120 °C View Scheme |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: amin-salt; dild. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: amin-salt; dild. acids; |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
Multi-step reaction with 3 steps 1: mineral acids 3: mineral acids View Scheme |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
Multi-step reaction with 3 steps 1: mineral acids 3: mineral acids View Scheme |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: Ag-salt; dild. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
Multi-step reaction with 3 steps 1: mineral acids 3: mineral acids View Scheme |
sulfadiazine
Conditions | Yield |
---|---|
With mineral acids byproducts: Ag-salt; concd. acids; | |
With mineral acids byproducts: Ag-salt; concd. acids; | |
Multi-step reaction with 3 steps 1: mineral acids 3: mineral acids View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 100 °C 2: palladium 10% on activated carbon / methanol; ethyl acetate; tetrahydrofuran / 50 °C / 37503.8 Torr View Scheme |
silver sulfadiazine
sulfadiazine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: mineral acids View Scheme | |
Multi-step reaction with 2 steps 2: mineral acids View Scheme | |
Multi-step reaction with 2 steps 2: mineral acids View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone for 3h; Darkness; | 97% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 4h; Reflux; | 96.3% |
In ethanol for 2.5h; Schiff Reaction; Reflux; | 62% |
sulfadiazine
water
cobalt(II) diacetate tetrahydrate
[cobalt(II)(sulfadiazine(-1H))2(H2O)2]
Conditions | Yield |
---|---|
In water byproducts: Na acetate; Na salt of ligand dissolved in H2O; Co salt in H2O added dropwise with stirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.; | 96% |
Conditions | Yield |
---|---|
In water byproducts: NaCl; Na salt of ligand dissolved in H2O; Co salt in H2O added dropwise with stirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.; | 96% |
sulfadiazine
ethyl acetoacetate
3-oxo-N-{4-[(pyrimidin-2-ylamino)sulphonyl]phenyl}butanamide
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 3h; | 95% |
at 140℃; for 0.25h; | 75% |
methanol
sulfadiazine
cobalt(II) diacetate tetrahydrate
[cobalt(II)(sulfadiazine(-1H))2(methanol)2]
Conditions | Yield |
---|---|
In methanol byproducts: Na acetate; Na salt of ligand dissolved in MeOH; Co salt in MeOH added dropwise withstirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.; | 95% |
Conditions | Yield |
---|---|
In methanol byproducts: NaCl; Na salt of ligand dissolved in MeOH; Co salt in MeOH added dropwise withstirring at 40°C for 1 h; filtered; ppt. washed with H2O, MeOH and Et2O successively; dried under vac.; elem. anal.; | 95% |
1-oxa-4-aza-spiro[4.4]nonane
formaldehyd
sulfadiazine
C18H23N5O3S
Conditions | Yield |
---|---|
In ethanol; water for 4h; Reflux; | 95% |
sulfadiazine
1-n-butyl-3-methylimidazolim bromide
C8H15N2(1+)*C10H9N4O2S(1-)
Conditions | Yield |
---|---|
Stage #1: 1-n-butyl-3-methylimidazolim bromide With Merck ion exchange resin III In water Stage #2: sulfadiazine In water at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With acetic acid at 120℃; for 0.166667h; | 94% |
sulfadiazine
Conditions | Yield |
---|---|
Stage #1: sulfadiazine With sulfuric acid; sodium nitrite In water at 0 - 5℃; for 0.25h; Stage #2: (E)-N-[(2-chloroquinolin-3-yl)methylene]-4-phenylthiazol-2-amine With sodium hydroxide In ethanol; water for 1h; pH=5 - 6; Cooling with ice; | 93% |
sulfadiazine
n-hexadecanoyl chloride
N-palmitoyl-sulfanilic acid pyrimidin-2-ylamide
Conditions | Yield |
---|---|
With pyridine for 48h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In ethanol at 0 - 5℃; Stage #2: 2-Mercaptobenzothiazole With sodium hydroxide In ethanol at 5 - 20℃; for 6h; | 92% |
N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine
sulfadiazine
4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(pyrimidin-2-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 85℃; | 92% |
Conditions | Yield |
---|---|
Stage #1: 1-octyl-3-methyl-imidazolium bromide With Merck ion exchange resin III In water Stage #2: sulfadiazine In water at 20℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 91% |
sulfadiazine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 10 - 50℃; for 3h; | 91% |
sulfadiazine
Conditions | Yield |
---|---|
With water In acetone react. at 75°C for 1 h; ppt.; elem. anal.; | 90% |
With water In methanol react. at 75°C for 1 h; ppt.; elem. anal.; | 90% |
sulfadiazine
Conditions | Yield |
---|---|
With water In methanol react. at 60°C; pptn. after several hours; filtration (glass filter); washing of the ppt. with MeOH, H2O, EtOH and ether; elem. anal.; | 90% |
Conditions | Yield |
---|---|
In methanol; water mixt. Cu(2+) salt and ligand was dissolved in MeOH, concd. ammonia soln.was added dropwise and stirred for 10 min; slow evapn. at room temp.; elem. anal.; | 90% |
Conditions | Yield |
---|---|
In methanol; water mixt. Cu(2+) salt and ligand was dissolved in MeOH, concd. ammonia soln.was added dropwise and stirred for 10 min; slow evapn. at room temp.; elem. anal.; | 90% |
4-fluorocinnamic acid
sulfadiazine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Reflux; | 90% |
sulfadiazine
acetylacetone
4-{2-[2,4-dioxopentan-3-ylidene]hydrazinyl}-N-(pyrimidin-2-yl)benzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In water; acetic acid at 0 - 5℃; Stage #2: acetylacetone With sodium acetate In ethanol; water; acetic acid at 0 - 20℃; for 2h; | 90% |
sulfadiazine
3-methyl-1-tosyl-1H-pyrazol-5(4H)-one
Conditions | Yield |
---|---|
With hydrogenchloride; sodium acetate; sodium nitrite In ethanol; water at 0 - 5℃; for 1h; | 90% |
Conditions | Yield |
---|---|
Stage #1: sulfadiazine With hydrogenchloride; sodium nitrite In water at 0 - 70℃; for 0.0833333h; Stage #2: 1H-benzimidazol-2-acetonitrile With sodium acetate In ethanol at 0 - 5℃; | 90% |
Conditions | Yield |
---|---|
Stage #1: 2-aminopyrimidine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: sulfadiazine With sodium hydroxide In water at 0 - 5℃; pH=7; | 89.5% |
Reported in EPA TSCA Inventory.
The Sulfadiazine, with the CAS registry number 68-35-9, is also known as Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-. It belongs to the product categories of Antibiotics for Research and Experimental Use; Biochemistry; Sulfonamides (Antibiotics for Research and Experimental Use). Its EINECS registry number is 200-685-8. This chemical's molecular formula is C10H10N4O2S and molecular weight is 250.277. Its IUPAC name is called 4-amino-N-pyrimidin-2-ylbenzenesulfonamide. Side effects reported for sulfadiazine include: nausea, upset stomach, loss of appetite, and dizziness. This chemical's classification codes are Anti-infective Agents; Antibacterial; Antiparasitic Agents; Antiprotozoal agents; Coccidiostats; Drug / Therapeutic Agent; Human Data; Reproductive Effect.
Physical properties of Sulfadiazine: (1)ACD/LogP: -0.12; (2)ACD/LogD (pH 5.5): -0.13; (3)ACD/LogD (pH 7.4): -0.66; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 19.93; (7)ACD/KOC (pH 7.4): 5.87; (8)#H bond acceptors: 6; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.679; (12)Molar Refractivity: 63.14 cm3; (13)Molar Volume: 167.2 cm3; (14)Surface Tension: 82.6 dyne/cm; (15)Density: 1.496 g/cm3; (16)Flash Point: 263.8 °C; (17)Enthalpy of Vaporization: 78.38 kJ/mol; (18)Boiling Point: 512.6 °C at 760 mmHg; (19)Vapour Pressure: 1.28E-10 mmHg at 25°C.
Preparation of Sulfadiazine: this chemical can be prepared by chaff iodate and nitro metformin. This reaction will need reagents acetyl groups benzene sulfo-chloride and pyridine.
Uses of Sulfadiazine: It eliminates bacteria that cause infections by stopping the production of folic acid inside the bacterial cell, and is commonly used to treat urinary tract infections (UTIs). In combination, sulfadiazine and pyrimethamine, can be used to treat toxoplasmosis, a disease caused by Toxoplasma gondii.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
(2)InChI: InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,; (3)16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
(4)InChIKey: SEEPANYCNGTZFQ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | TDLo | oral | 1800mg/kg/5D- (1800mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" KIDNEY, URETER, AND BLADDER: HEMATURIA ENDOCRINE: HYPOGLYCEMIA | Postgraduate Medical Journal. Vol. 53, Pg. 103, 1977. |
child | TDLo | unreported | 138mg/kg (138mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC KIDNEY, URETER, AND BLADDER: HEMATURIA KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Postgraduate Medical Journal. Vol. 53, Pg. 103, 1977. |
dog | LD | oral | > 5gm/kg (5000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 79, Pg. 354, 1943. | |
man | TDLo | oral | 229mg/kg/8D-I (229mg/kg) | GASTROINTESTINAL: OTHER CHANGES KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Israel Journal of Medical Sciences. Vol. 6, Pg. 561, 1970. |
mouse | LD50 | intraperitoneal | 750mg/kg (750mg/kg) | "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 109, 1969. | |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03347, | |
mouse | LD50 | oral | 1500mg/kg (1500mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 571, 1971. | |
mouse | LD50 | subcutaneous | 1600mg/kg (1600mg/kg) | Drugs in Japan Vol. 6, Pg. 386, 1982. | |
rat | LD50 | intravenous | 880mg/kg (880mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950. | |
rat | LDLo | intraperitoneal | 446mg/kg (446mg/kg) | Klinische Wochenscrift. Vol. 27, Pg. 449, 1949 |
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