1220-83-3

Basic information

• Product Name: Sulfamonomethoxine
• Synonyms: 4-azanyl-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide;Sulfamonomethoxine,4-Amino-N-(6-methoxy-4-pyrimidinyl)benzenesulfonamide;4-Methoxy-6-sulfanilaMidopyriMidine;4-SulfanilaMido-6-MethoxypyriMidine;6-Methoxy-4-sulfanilaMidopyriMidine;4-Amino-N-(6-methoxy-4-pyrimidinyl)benzenesulfonamide N-(6-Methoxy-4-pyrimidinyl)sulfanilamide;SulfaMonoMethoxine,SMM,SulfaMonoMethoxine sodiuM;N1-(6-Methoxy-4-pyrimidinyl)sulfanilamide
• CAS NO: 1220-83-3
• Molecular Formula: C₁₁H₁₂N₄O₃S
• Molecular Weight: 280.3
• EINECS: 1806241-263-5
• Product Categories: Amines;Aromatics;Inhibitor;PROSULFA;Heterocyclic Compounds;Heterocycles;Sulfur & Selenium Compounds
• Mol File: 1220-83-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 203-2060C
• Boiling Point: 513℃
• Flash Point: >110°(230°F)
• Appearance: white to white with yellow cast/
• Density: 1.3936 (rough estimate)
• Vapor Pressure: 1.2E-10mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: 0-6°C
• Solubility: methanol: soluble10mg/mL
• PKA: pKa 5.94 (Uncertain)
• Water Solubility: Soluble in water at 10mg/ml with warming. Also soluble in ethanol or methanol
• BRN: 621128
• CAS DataBase Reference: Sulfamonomethoxine(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfamonomethoxine(1220-83-3)
• EPA Substance Registry System: Sulfamonomethoxine(1220-83-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: WP0550000
• HazardClass: IRRITANT
• Hazardous Substances Data: 1220-83-3(Hazardous Substances Data)

Usage

Chemical Properties

White To Off-White Crystalline Powder

Uses

Different sources of media describe the Uses of 1220-83-3 differently. You can refer to the following data:
1. Protein binding. Inhibitor of enzyme. Sulfamonomethoxine and Trimethoprim
2. antibacterial
3. Protein binding. Inhibitor of enzyme. Sulfamonomethoxine and Trimethoprim are used for treating porcine unknown hyperpyrexia.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 2764, 1961 DOI: 10.1021/jo01066a034

Biochem/physiol Actions

Sulfamonomethoxine is a competitive inhibitor of dihydropteroate synthetase used to block the synthesis of folic acid.

InChI:InChI=1/C11H12N4O3S/c1-18-11-6-10(13-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,14,15)

Synthetic route

4-Nitrobenzenesulfonamido-6-methoxypyrimidine (1748-50-1) → sulfamonomethoxine (1220-83-3)

Conditions	Yield
With iron; ammonium chloride In water for 10h; Heating; Yield given;

4-nitrobenzenediazonium chloride (100-05-0) + benzothiophen-3-yl-glyoxal phenylhydrazone → sulfamonomethoxine (1220-83-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: SO2 / CuSO4 / acetic acid / 6 - 20 °C 2: 92 percent / pyridine / 2 h / 56 - 58 °C 3: Fe, NH4Cl / H2O / 10 h / Heating View Scheme

4-Nitrobenzenesulfonyl chloride (98-74-8) + (+-)-2-amino-5-butyl-thiazol-4-one → sulfamonomethoxine (1220-83-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 2 h / 56 - 58 °C 2: Fe, NH4Cl / H2O / 10 h / Heating View Scheme

2,4,6-trimethylpyrylium chlorate(VII) (940-93-2) + sulfamonomethoxine (1220-83-3) → 1-[4-(6-Methoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-trimethyl-pyridinium; perchlorate

Conditions	Yield
In acetic acid for 2h; Heating;	97%

sulfamonomethoxine (1220-83-3) + glycyrrhyzic acid → C75H92N12O22S3

Conditions	Yield
pyridine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20 - 22℃; for 24h; Condensation;	90.4%

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5, 42996-84-9) + sulfamonomethoxine (1220-83-3) → p-methoxycinnamoyl sulfamonomethoxine

Conditions	Yield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;	85%

sulfamonomethoxine (1220-83-3) → 1,3-bis(N1-4-amino-6-methoxypyrimidinebenzenesulfonamide)-2,2,2,4,4,4-hexa-chlorocyclodiphosph(V)azane

Conditions	Yield
With phosphorus pentachloride In benzene at 15℃; for 0.5h;	81%

2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate (63673-58-5) + sulfamonomethoxine (1220-83-3) → 4-(2,6-dimethyl-4-oxo-5-phenyl-4H-pyrimidin-1-yl)-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions	Yield
In acetic acid for 48h; Ambient temperature;	65%

sulfamonomethoxine (1220-83-3) + (3R,5aS,6R,9R,10S,12R,12aR)-10-(3-bromopropoxy)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene (165068-34-8) → 4-amino-N-(6-methoxypyrimidin-4-yl)-N-(3-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)propyl)benzenesulfonamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	56%

3-(o-methoxyphenyl)-2,6-dimethyl-4-oxo-1,3-oxazinium perchlorate + sulfamonomethoxine (1220-83-3) → 4-[5-(2-methoxy-phenyl)-2,6-dimethyl-4-oxo-4H-pyrimidin-1-yl]-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions	Yield
In acetic acid for 48h; Ambient temperature;	35%

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + sulfamonomethoxine (1220-83-3) → (Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)-N-(4-(N-(6-methoxypyrimidin-4-yl)sulfamoyl)phenyl)acetamide

Conditions	Yield
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere;	32.7%

sulfamonomethoxine (1220-83-3) → 4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide (14762-26-6)

Conditions	Yield
With sodium hydroxide for 14h; Heating;	16%
With sodium hydroxide at 80 - 90℃; for 50h; Yield given;

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + sulfamonomethoxine (1220-83-3) → C36H30N8O8S4

Conditions	Yield
With pyridine In 1,4-dioxane Ambient temperature;

tropaeolin O + sulfamonomethoxine (1220-83-3) → C23H18N7O8S2(1-)*Na(1+) (1312665-65-8)

Conditions	Yield
Stage #1: sulfamonomethoxine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

4-acetoxyferuloyl chloride (55882-65-0, 108608-07-7, 50906-12-2) + sulfamonomethoxine (1220-83-3) → C23H22N4O7S

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 6h;

4-acetoxyferuloyl chloride (55882-65-0, 108608-07-7, 50906-12-2) + sulfamonomethoxine (1220-83-3) → N1-feruloylsulfamonomethoxine

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 6 h / 0 - 20 °C 2: hydrogenchloride / tetrahydrofuran / 1 h / 60 °C View Scheme

p-acetoxycinnamoyl chloride (53901-95-4, 108608-06-6, 58523-18-5) + sulfamonomethoxine (1220-83-3) → 4-acetoxycinnamoyl sulfamonomethoxine

Conditions	Yield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;

Upstream product

• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 1748-50-1 4-Nitrobenzenesulfonamido-6-methoxypyrimidine 

Downstream Products

• 1312665-65-8 C₂₃H₁₈N₇O₈S₂^(1-)*Na⁽¹⁺⁾ 
• 14762-26-6 4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide 

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