74863-82-4

Basic information

• Product Name: 3-Methyl-8-quinolinesulphonyl chloride
• Synonyms: 3-METHYL-8-QUINOLINESULFONYL CHLORIDE;3-METHYL-8-QUINOLINE SULPHONYL CHLORIDE;8-CHLOROSULFONYL-3-METHYLQUINOLINE;3-methyl quinoline-8-sulphonyl chloride;8-Quinolinesulfonylchloride,3-methyl-(9CI);3-Methyl-8-quinolinesulphonyl chloride 95%;3-Methyl-8-quinolinesulfonyl chloride ,98%;Argatroban Impurity 29
• CAS NO: 74863-82-4
• Molecular Formula: C₁₀H₈ClNO₂S
• Molecular Weight: 241.69
• EINECS: -0
• Product Categories: SULFONYLHALIDE;Aromatics Compounds;Aromatics;Sulfonyl Chlorides;Sulfur & Selenium Compounds
• Mol File: 74863-82-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 158-159°C
• Boiling Point: 371.5 °C at 760 mmHg
• Flash Point: 178.5 °C
• Appearance: /
• Density: 1.424 g/cm³
• Vapor Pressure: 2.19E-05mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• PKA: 0.82±0.28(Predicted)
• Stability: Moisture Sensitive - Store Under Inert Atmosphere
• CAS DataBase Reference: 3-Methyl-8-quinolinesulphonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-8-quinolinesulphonyl chloride(74863-82-4)
• EPA Substance Registry System: 3-Methyl-8-quinolinesulphonyl chloride(74863-82-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25
• Hazardous Substances Data: 74863-82-4(Hazardous Substances Data)

Usage

Uses

3-Methyl-8-quinolinesulfonyl Chloride (cas# 74863-82-4) is a compound useful in organic synthesis.

InChI:InChI=1/C10H8ClNO2S/c1-7-5-8-3-2-4-9(15(11,13)14)10(8)12-6-7/h2-6H,1H3

Synthetic route

3-methylquinoline (612-58-8) → 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4)

Conditions	Yield
With chlorosulfonic acid; thionyl chloride In water	1.58 g (18%)

3-methyl-8-quinolinesulfonic acid (153886-69-2) → 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4)

Conditions	Yield
With bis(trichloromethyl) carbonate; triethylamine In toluene at 25 - 40℃; for 3h; Reagent/catalyst; Temperature;	178 g

C22H26N4O6 + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → Nω,Nω'-bis((benzyloxy)carbonyl)-N2-((3-methylquinolin-8-yl)sulfon-yl)-L-arginine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; water at 0 - 20℃; for 16h;	98%

N-nitro-L-arginine (2149-70-4) + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → C16H20N6O6S

Conditions	Yield
With sodium carbonate; potassium hydroxide In methanol; water at 0 - 20℃; Concentration; Reagent/catalyst; Solvent;	96.12%

(2R,4R)-1-[N-nitro-L-arginyl]-4-methyl-2-piperidinecarboxylic acid ethyl ester + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → C25H35N7O7S

Conditions	Yield
With potassium carbonate; potassium hydroxide In ethanol; water at 0 - 20℃; Concentration; Reagent/catalyst; Solvent;	96.09%

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + (3S,6S,9aS)-6-Carboxyamino-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester → (3S,6S,9aS)-6-(3-Methyl-quinoline-8-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carboxylic acid tert-butyl ester (188126-78-5)

Conditions	Yield
With triethylamine In dichloromethane	89%

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C20H30N6O5*ClH → C30H37N7O7S (367952-84-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	86%

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + (2R,4R)-1-((S)-2-Amino-5-benzyloxycarbonylamino-pentanoyl)-4-methyl-piperidine-2-carboxylic acid ethyl ester (174699-02-6) → (2R,4R)-1-[(S)-5-Benzyloxycarbonylamino-2-(3-methyl-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester (174699-04-8)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2.75h; Acylation;	75%

L-arginine (74-79-3) + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → 5-guanidino-2(S)-[1-(3-methylquinolyl)sulfonylamino]pentanoic acid (252985-90-3)

Conditions	Yield
With potassium carbonate In 1,4-dioxane; water at 20℃; for 2h; sulfonylation;	60%

C15H28N4O4 + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → C25H35N5O6S

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	10.21%

4-methoxy-3-amino-1,2-benzisoxazole (177995-40-3) + 8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) → N-(4-methoxybenzo[d]isoxazol-3-yl)-3-methylquinoline-8-sulfonamide

Conditions	Yield
Stage #1: 4-methoxy-3-amino-1,2-benzisoxazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.166667h; Stage #2: 8-(chlorosulphonyl)-3-methylquinoline In N,N-dimethyl-formamide; mineral oil for 16h;	8%

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + (2R,4R)-1-((S)-2-Amino-5-benzyloxycarbonylamino-4,4-difluoro-pentanoyl)-4-methyl-piperidine-2-carboxylic acid ethyl ester → (2R,4R)-1-[(S)-5-Benzyloxycarbonylamino-4,4-difluoro-2-(3-methyl-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester (183679-14-3)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h; Acylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + (S)-2-Amino-4-hydroxy-butyric acid benzhydryl ester; compound with toluene-4-sulfonic acid → (S)-4-Hydroxy-2-(3-methyl-quinoline-8-sulfonylamino)-butyric acid benzhydryl ester (183679-06-3)

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; Acylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C13H25ClN6O3*ClH → C23H32ClN7O5S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H30N6O4*ClH → C25H37N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H30N6O4*ClH → C25H37N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H30N6O4*ClH → C25H37N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C14H26N6O5*ClH → C24H33N7O7S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C17H34N6O4*ClH → C27H41N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C16H32N6O4*ClH → C26H39N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C17H34N6O4*ClH → C27H41N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C16H32N6O4*ClH → C26H39N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + 2(S)-amino-5-(3-nitroguanidino)-1-[4-(2-acetoxyethyl)piperidin-1-yl]pentan-1-one hydrochloride → 3-methylquinoline-8-sulfonic acid {4-(3-nitroguanidino)-1(S)-[4-(2-acetoxyethyl)piperidin-1-ylcarbonyl]butyl}amide (252985-95-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H28N6O5*ClH → C25H35N7O7S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C17H34N6O4*ClH → C27H41N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H29N7O4*ClH → C25H36N8O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C15H28N6O5*ClH → C25H35N7O7S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C18H36N6O4*ClH → C28H43N7O6S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C19H36N6O6*ClH → C29H43N7O8S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C20H38N6O5*ClH → C30H45N7O7S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C18H33N7O6*ClH → C28H40N8O8S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

8-(chlorosulphonyl)-3-methylquinoline (74863-82-4) + C24H36N6O7*ClH → C34H43N7O9S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h; pH=9; sulfonylation;

Upstream product

• 153886-69-2 3-methyl-8-quinolinesulfonic acid 
• 612-58-8 3-methylquinoline 

Downstream Products

• 74863-84-6 argatroban 
• 188127-04-0 [Imino-((S)-3-{[(3S,6S,9aS)-6-(3-methyl-quinoline-8-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-2-oxo-piperidin-1-yl)-methyl]-carbamic acid benzyl ester 
• 196936-96-6 [((S)-2-Hydroxy-3-{[(3S,6S,9aS)-6-(3-methyl-quinoline-8-sulfonylamino)-5-oxo-octahydro-pyrrolo[1,2-a]azepine-3-carbonyl]-amino}-piperidin-1-yl)-imino-methyl]-carbamic acid benzyl ester 
• 174699-04-8 (2R,4R)-1-[(S)-5-Benzyloxycarbonylamino-2-(3-methyl-quinoline-8-sulfonylamino)-pentanoyl]-4-methyl-piperidine-2-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation method of 3-methylquinoline-8-sulfonyl chloride

The invention belongs to the field of fine chemical product production, and particularly relates to a preparation method of 3-methylquinoline-8-sulfonyl chloride, and the method comprises the following steps: (1) carrying out catalytic cyclization on 2-aminobenzene sulfonic acid serving as an initial raw material, propionaldehyde and paraformaldehyde in a deep eutectic solvent to obtain 3-methylquinoline-8-sulfonic acid; and (2) carrying out acylating chlorination on the generated 3-methylquinoline-8-sulfonic acid under the action of an organic alkali by using bis (trichloromethyl) carbonate as a chlorinating agent, thereby obtaining the 3-methylquinoline-8-sulfonyl chloride. The method has the advantages of simple operation process, easily available raw material, low cost, no generation of harmful gases in the whole process, meeting of safety and environmental protection requirements, and facilitation of large-scale production.

HETEROAROMATIC AND THIOHETEROAROMATIC SUBSTITUTED SULFONAMIDE THROMBIN INHIBITORS

Sulfonamide thrombin inhibitors are provided which have the structure STR1 including all stereoisomers thereof, wherein X is S or--CH 2--; m is 0, 1 or 2 when X is--S--or m is 0 when X is--CH. sub.2--; n is 1, 2 or 3; R 1 and R 2 are independently H, lower alkyl, cyclo-alkyl, aryl, heteroaryl or heteroarylalkyl, or R 1 and R 2 can be taken together with the N atom to which they are attached to form a 5-to 8-membered ring which may optionally contain an additional N, O or S atom in the ring; R. sup.3 is heteroaryl; and R 4 is alkyl, cycloalkyl, aryl, heteroaryl, quinolinyl or tetrahydroquinolinyl, and pharmaceutically acceptable salts thereof.