59-40-5

Basic information

• Product Name: Sulfaquinoxaline
• Synonyms: SULFABENZPYRAZINE;SULFACHINOXALIN;SULFACHINOXALINE;sulfa-q 20;SULFAQUINOXALIN;SULFAQUINOXALINE;N-(2-QUINOXALINYL)SULFANILAMIDE;N'-2-QUINOXALYL SULFANILAMINE
• CAS NO: 59-40-5
• Molecular Formula: C₁₄H₁₂N₄O₂S
• Molecular Weight: 300.34
• EINECS: 213-526-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Amines;Aromatics;NULL;PHENERGAN
• Mol File: 59-40-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 247-2480C
• Boiling Point: 551.1 °C at 760 mmHg
• Flash Point: 287.1 °C
• Appearance: light yellow crystalline powder
• Density: 1.3196 (rough estimate)
• Vapor Pressure: 3.42E-12mmHg at 25°C
• Refractive Index: 1.6440 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 5.65±0.10(Predicted)
• Merck: 13,9025
• BRN: 290026
• CAS DataBase Reference: Sulfaquinoxaline(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfaquinoxaline(59-40-5)
• EPA Substance Registry System: Sulfaquinoxaline(59-40-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-42/43
• Safety Statements: 22-36/37-45
• WGK Germany: 3
• RTECS: WP2100000
• Hazardous Substances Data: 59-40-5(Hazardous Substances Data)

Usage

Description

Sulfaquinoxaline is a kind of veterinary medicine which can be used for the treatment of coccidiosis in cattle and sheep. It is usually used in combination with Amprolium and Vitamin K. It is a protective agent against upper respiratory infections of poultry and a prophylactic against coccidiosis. It takes effects via inhibiting vitamin K epoxidase (epoxide reductase, menadione epoxide reductase) and quinone reductase. Sulfaquinoxaline played an important part in the demotion of roast chicken from vaunted Sunday-dinner status to an un-respected position on the everyday menu of the Western world. Although it has long been eclipsed by other drugs in poultry management, it continues to be used in other host species.

Brand Name(s) in US

Sulfa-Nox

Reference

Campbell, W. C. "History of the discovery of sulfaquinoxaline as a coccidiostat." Journal of Parasitology 94.4(2008):934-945.

Chemical Properties

Crystalline Solid

InChI:InChI=1/C14H11N4O2S.Na/c15-10-5-7-11(8-6-10)21(19,20)18-14-9-16-12-3-1-2-4-13(12)17-14;/h1-9H,15H2;/q-1;+1

Synthetic route

sulfanilamide (63-74-1) + chloroacetic acid (79-11-8) + 1,2-diamino-benzene (95-54-5) → sulphaquinoxaline (59-40-5)

Conditions	Yield
Stage #1: chloroacetic acid; 1,2-diamino-benzene With N'-methyl-N-heptylimidazolium hydroxide salt at 100℃; for 2h; Stage #2: sulfanilamide With trichlorophosphate at 100℃; for 3h; Concentration; Temperature;	93%

N-[4-(quinoxalin-2-ylsulfamoyl)phenyl]acetamide (6632-67-3) → sulphaquinoxaline (59-40-5)

Conditions	Yield
With sodium hydroxide In water for 2h; Heating;	91.2%
With hydrogenchloride; ethanol; water

2-chloroquinoxaline (1448-87-9) + sulfanilamide (63-74-1) → sulphaquinoxaline (59-40-5)

quinoxalin-2-ylamine (5424-05-5) → sulphaquinoxaline (59-40-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 31.6 percent / pyridine / 25 °C 2: 91.2 percent / NaOH / H2O / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: pyridine 2: water; ethanol; HCl View Scheme

p-acetylaminobenzenesulfonyl chloride (121-60-8) + 4-acetoxy-N1-acetyl-o-phenylenediamine → sulphaquinoxaline (59-40-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 31.6 percent / pyridine / 25 °C 2: 91.2 percent / NaOH / H2O / 2 h / Heating View Scheme

2-aminoquinoxaline-3-carboxylic acid (85414-82-0) → sulphaquinoxaline (59-40-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitrobenzene 2: pyridine 3: water; ethanol; HCl View Scheme

p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulphaquinoxaline (59-40-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: water; ethanol; HCl View Scheme

alloxazine (490-59-5) → sulphaquinoxaline (59-40-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; H2SO4 2: pyridine 3: water; ethanol; HCl View Scheme
Multi-step reaction with 4 steps 1: water; NH3 / 175 °C 2: nitrobenzene 3: pyridine 4: water; ethanol; HCl View Scheme

sulphaquinoxaline (59-40-5) + diazepam (439-14-5) → 4-([4-{7-chloro-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl}phenyl]diazenyl)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
Stage #1: sulphaquinoxaline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.0833333h; Green chemistry; Stage #2: diazepam With sodium acetate In ethanol; water Green chemistry;	90%

thiophosgene (463-71-8) + sulphaquinoxaline (59-40-5) → 4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide (681235-15-4)

Conditions	Yield
In water for 1h;	86%

4-isothiocyanato-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide (1148108-83-1) + sulphaquinoxaline (59-40-5) → N-(1-phenyl-1H-pyrazol-5-yl)-4-(3-(4-(N-quinoxalin-2-ylsulfamoyl)phenyl)thioureido)benzenesulfonamide (1148108-99-9)

Conditions	Yield
With triethylamine In 1,4-dioxane for 2h; Reflux;	85%

4-chlorobenzoquinazoline (33987-02-9) + sulphaquinoxaline (59-40-5) → 4-(benzo[g]quinazolin-4-ylamino)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 24h; Reflux;	84%

sulphaquinoxaline (59-40-5) + ((E)-3-(3-(dimethylamino)acryloyl))-2H-chromen-2-one (371756-61-5) → (Z)-4-(3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-enylamino)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
In ethanol for 21h; Reflux;	78%

sulphaquinoxaline (59-40-5) + (Z)-3-(dimethylamino)-1-(10H-phenothiazin-2-yl)prop-2-en-1-one → (Z)-4-(3-oxo-3-(10H-phenothiazine-2yl)prop-1-enylamino)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
In ethanol for 18h; Reflux;	78%

2-chloro-6-methylnicotinonitrile (28900-10-9) + sulphaquinoxaline (59-40-5) → 4-(3-cyano-6-methylpyridin-2-ylamino)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide for 18h; Reflux;	77%

4-chloro-2-phenylquinazoline (6484-25-9) + sulphaquinoxaline (59-40-5) → 4-(2-phenylquinazolin-4-ylamino)-N-(quinoxalin2-yl)benzenesulfonamide

Conditions	Yield
In N,N-dimethyl-formamide for 22h; Reflux;	76%

sulphaquinoxaline (59-40-5) + orthoformic acid triethyl ester (122-51-0) + malononitrile (109-77-3) → 4-(2,2-dicyanovinylamino)-N-(quinoxalin-2-yl)benzensulfonamide (1314583-28-2)

Conditions	Yield
With acetic acid In methanol for 5h; Reflux;	65%

sulphaquinoxaline (59-40-5) + 1-bromo-3-(10β-dihydroartemisinoxy)propane (165068-34-8) → 4-amino-N-(quinoxalin-2-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 8h;	51%

sulphaquinoxaline (59-40-5) + orthoformic acid triethyl ester (122-51-0) + ethyl 2-cyanoacetate (105-56-6) → C20H17N5O4S (1314583-29-3)

Conditions	Yield
With acetic acid In methanol for 5h; Reflux;	50%

sulphaquinoxaline (59-40-5) + 1-bromo-2-(10β-dihydroartemisinoxy)ethane (101834-30-4) → 4-amino-N-(quinoxalin-2-yl)-N-(2-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)ethyl)benzenesulfonamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 17h;	50%

sulphaquinoxaline (59-40-5) + cantharidin (56-25-7) → N-cantharidinimidosulfaquinoxaline

Conditions	Yield
With triethylamine In toluene at 200℃; for 2h; Sealed tube; High pressure;	6%

succinic acid anhydride (108-30-5) + sulphaquinoxaline (59-40-5) → N-(4-quinoxalin-2-ylsulfamoyl-phenyl)-succinamic acid (119059-57-3)

sulphaquinoxaline (59-40-5) + benzoyl chloride (98-88-4) → 4-benzamido-N-(quinoxalin-2-yl)benzenesulfonamide

sulphaquinoxaline (59-40-5) + Hexanoyl chloride (142-61-0) → N-hexanoyl-sulfanilic acid quinoxalin-2-ylamide

sulphaquinoxaline (59-40-5) + ethyl 2,3-dioxobutyrate (1723-25-7) → ethyl 2,3-dioxobutyrate-2-<(N1-2-quinoxalyl)sulfonamidophenyl>hydrazone (74731-82-1)

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite 1.) water; 2.) ethanol; Yield given. Multistep reaction;

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + sulphaquinoxaline (59-40-5) → C42H30N8O6S4

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

2-(3-bromo-phenyl)-quinoline-4-carbonyl chloride (883526-03-2) + sulphaquinoxaline (59-40-5) → 2-(3-bromo-phenyl)-quinoline-4-carboxylic acid [4-(quinoxalin-2-ylsulfamoyl)-phenyl]-amide

Conditions	Yield
With pyridine at 25℃;

sulphaquinoxaline (59-40-5) + 2,4-dichlorobenzoyl chloride (89-75-8) → 2,4-dichloro-N-[4-(quinoxalin-2-ylsulfamoyl)-phenyl]-benzamide

Conditions	Yield
With pyridine at 25℃;

sulphaquinoxaline (59-40-5) + 4-chlorophenacetyl chloride (25026-34-0) → 2-(4-chloro-phenyl)-N-[4-(quinoxalin-2-ylsulfamoyl)-phenyl]-acetamide

Conditions	Yield
With pyridine at 25℃;

sulphaquinoxaline (59-40-5) + hydrocinnamic acid chloride (645-45-4) → 4-(3-phenylpropionamido)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
With pyridine at 25℃;

sulphaquinoxaline (59-40-5) + 2,4-dichlorophenylacetyl chloride (53056-20-5) → 4-(2,4-dichlorophenylacetamido)-N-(quinoxalin-2-yl)benzenesulfonamide

Conditions	Yield
With pyridine at 25℃;

sulphaquinoxaline (59-40-5) → 4-(3-oxo-3H-benzo[d]isothiazol-2-yl)-N-quinoxalin-2-yl-benzenesulfonamide

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dioxane / Ambient temperature 2: N-bromosuccinimide, pyridine / dioxane / 3 h / Ambient temperature View Scheme

Upstream product

• 1448-87-9 2-chloroquinoxaline 
• 63-74-1 sulfanilamide 
• 6632-67-3 N-[4-(quinoxalin-2-ylsulfamoyl)phenyl]acetamide 
• 5424-05-5 quinoxalin-2-ylamine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 85414-82-0 2-aminoquinoxaline-3-carboxylic acid 
• 490-59-5 alloxazine 
• 79-11-8 chloroacetic acid 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 119059-57-3 N-(4-quinoxalin-2-ylsulfamoyl-phenyl)-succinamic acid 
• 74731-82-1 ethyl 2,3-dioxobutyrate-2-<(N¹-2-quinoxalyl)sulfonamidophenyl>hydrazone 
• 1314583-36-2 4-((3-amino-5-imino-1-phenyl-1H-pyrazol-4-ylidene)methylamino)-N-(quinoxalin-2-yl)benzenesulfonamide 
• 1314583-37-3 4-((3-amino-5-oxo-1-phenyl-1H-pyrazol-4-ylidene)methylamino)-N-(quinoxalin-2-yl)benzenesulfonamide 
• 1314583-29-3 C₂₀H₁₇N₅O₄S 
• 1314583-28-2 4-(2,2-dicyanovinylamino)-N-(quinoxalin-2-yl)benzensulfonamide 
• 681235-15-4 4-isothiocyanato-N-quinoxaline-2-yl-benzenesulfonamide 

Relevant articles and documents

Preparation method of sulfaquinoxaline

The invention discloses a preparation method of sulfaquinoxaline. The preparation method comprises the following steps: mixing o-phenylenediamine, chloroacetic acid, an alkaline ionic liquid and a solid base catalyst; under the condition of continuously blowing in air, carrying out reaction for 1-5 hours at 80-150 DEG C; after the reaction, stopping blowing in air, and adding phosphorus oxychloride and p-amino-benzene sulfonamide to carry out reaction continuously for 1-3 hours at 80-150 DEG C; and carrying out separation and purification on a reaction liquid to obtain sulfaquinoxaline. The preparation method disclosed by the invention is easy to operate, has low requirements on reaction equipment and causes little pollution to the environment, the product is easy to separate, and the ionic liquid and solid base can be used repeatedly, so that the preparation method is an economical, practical, and environment-friendly technology.

Process for formulating a synthetic drug for use in animal feed, and resulting formulation

A method of formulating a synthetic drug for use in animal feed, for the purpose of reducing carry-over of the synthetic drug to subsequent lots of animal feed in the feed mill.