137-47-3

Basic information

• Product Name: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE
• Synonyms: 4-CHLORO-N,N'-DIMETHYL-3-NITRO-BENZENE SULFONAMIDE;4-CHLORO-N,N-DIMETHYL-3-NITRO-BENZENESULFONAMIDE;2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE;4-chloro-n,n-dimethyl-3-nitro-benzenesulfonamid;4-chloro-N,N-dimethyl-3-nitrobenzenesulphonamide;4-chloro-3-nitro-N,N-dimethylbenzenesulfonamide;4-CHLORO-3-NITRO-N,N-DIMETHYLBENZENESULFAMIDE;N,N-DIMETHYL-4-CHLORO-3-NITROBENZENE SULFONAMIDE
• CAS NO: 137-47-3
• Molecular Formula: C₈H₉ClN₂O₄S
• Molecular Weight: 264.69
• EINECS: 205-295-1
• Mol File: 137-47-3.mol

Chemical Properties

• Melting Point: 103.5℃ (acetone water )
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 188 °C
• Appearance: /
• Density: 1.48 g/cm³
• Vapor Pressure: 3.32E-06mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(137-47-3)
• EPA Substance Registry System: 2-NITROCHLOROBENZENE-4-(N,N-DIMETHYL)-SULPHONAMIDE(137-47-3)

Safety Data

• Hazardous Substances Data: 137-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9ClN2O4S/c1-10(2)16(14,15)6-3-4-7(9)8(5-6)11(12)13/h3-5H,1-2H3

Synthetic route

3-(Dimethylaminomethyl)indole (87-52-5) + 3-nitro-4-chlorosulfonyl chloride (97-08-5) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With triethylamine In acetonitrile at 25℃; for 24h;	84%
With triethylamine In acetonitrile at 25℃; for 24h;	84%

3-nitro-4-chlorosulfonyl chloride (97-08-5) + dimethyl amine (124-40-3) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
In tetrahydrofuran	20%

3-nitro-4-chlorosulfonyl chloride (97-08-5) + N,N-dimethylammonium chloride (506-59-2) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 20℃; for 2h;

3-nitro-4-chlorosulfonyl chloride (97-08-5) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With dimethyl amine In water; toluene

diethyl ether (60-29-7) + 2-chloro-3-nitrobenzenesulfonyl chloride (15945-25-2) → 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3)

Conditions	Yield
With dimethyl amine In methanol; water

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-hydroxy-5-tert-butylisoxazole (107403-12-3) → 5-t-butyl-2-(4-dimethylsulfamoyl-2-nitrophenyl)-4-isoxazolin-3-one (118938-18-4)

Conditions	Yield
With hydrogenchloride; potassium carbonate In dimethyl sulfoxide	89.5%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + tert-butyl (3-(2-mercaptonicotinamido)propyl)carbamate → tert-butyl (3-(9-(N,N-dimethylsulfamoyl)-5-oxobenzo[b]pyrido-[3,2-f][1,4]thiazepin-6(5H)-yl)propyl)carbamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Smiles Aromatic Rearrangement;	89%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + Thiosalicylic acid (147-93-3) → 2-((4-(N,N-dimethylsulfamoyl)-2-nitrophenyl)thio)benzoic acid

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol for 18h; Reflux;	81%

2-(4,5-dihydro-1H-imidazol-2-yl)-benzenethiol (53440-31-6) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-dimethyl-2,3-dihydrodibenzo[b,f ]imidazo[1,2-d][1,4]-thiazepine-7-sulfonamide

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 75℃; Smiles Aromatic Rearrangement;	66%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-ethylamino propionitrile (21539-47-9) → 2-nitro-4-dimethylsulfamoyl-N-ethylaniline (81676-81-5) + 2-nitro-4-dimethylsulfamoyl-N-ethyl-N-β-cyanoethylaniline (81676-78-0)

Conditions	Yield
In methanol at 65℃; for 10h;	A 30% B 65%
In i-Amyl alcohol at 130℃; Product distribution; Mechanism; other temperature, time, solvent;

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-N, N-dimethyl-3-nitrobenzenesulfonamide (862298-40-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	37%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 1-amino-2-nitrobenzene-4-sulphonic acid dimethylamide (57824-29-0)

Conditions	Yield
With ammonia In methanol at 55℃;	16%

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3,3'-dinitro-4,4'-sulfanediyl-bis-benzenesulfonic acid bis-dimethylamide (101430-57-3)

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 4-Ethoxyaniline (156-43-4) → 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide (67338-59-4)

Conditions	Yield
With sodium hydrogencarbonate

Cyclohexanone oxime (100-64-1) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-Cyclohexylideneaminooxy-N,N-dimethyl-3-nitro-benzenesulfonamide (13181-80-1)

Conditions	Yield
With sodium ethanolate In 1,4-dioxane

3-methyl-butan-2-one oxime (600-20-4) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1,2-Dimethyl-prop-(E)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-09-7)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

(+/-)-camphor oxime (13559-66-5) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-Dimethyl-3-nitro-4-[1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneaminooxy]-benzenesulfonamide

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

3,5-dichloro-4-hydroxy-benzaldehyde-oxime (26879-81-2) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1-(3,5-Dichloro-4-hydroxy-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (61101-46-0)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

3,5-dibromo-4-hydroxy-benzaldehyde-oxime (25952-74-3) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[1-(3,5-Dibromo-4-hydroxy-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-06-4)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 4-hydroxy-3,5-diiodo-benzaldehyde-oxime (2296-76-6) → 4-[1-(4-Hydroxy-3,5-diiodo-phenyl)-meth-(Z)-ylideneaminooxy]-N,N-dimethyl-3-nitro-benzenesulfonamide (13194-07-5)

Conditions	Yield
With sodium ethanolate In ethanol; acetonitrile

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + di-n-propylamine (142-84-7) → Dipropyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-51-7)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + dimethyl amine (124-40-3) → Dimethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-49-3)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + diethylamine (109-89-7) → Diethyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-50-6)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + diisopropylamine (108-18-9) → Diisopropyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-52-8)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + N-cyclohexyl-cyclohexanamine (101-83-7) → Dicyclohexyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-53-9)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

carbon disulfide (75-15-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + dibenzylamine (103-49-1) → Dibenzyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester (25678-54-0)

Conditions	Yield
(i) NaOH, (ii) /BRN= 2945366/; Multistep reaction;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3-Nitro-4-methylamino-benzolsulfonsaeure-dimethylamid (68528-28-9) + 4-[(2-Cyano-ethyl)-methyl-amino]-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-73-5)

Conditions	Yield
In i-Amyl alcohol at 130℃; Product distribution; Mechanism; other temperature, time, solvent;

N-(2-cyanoethyl)-N-methylamine (693-05-0) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 4-[(2-Cyano-ethyl)-methyl-amino]-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-73-5)

Conditions	Yield
In methanol Heating;

3-diethylaminopropionitrile (5351-04-2) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → hydrochloride of 3-diethylaminopropionitrile (37899-75-5) + 4-Diethylamino-N,N-dimethyl-3-nitro-benzenesulfonamide (81676-68-8) + acrylonitrile (107-13-1)

Conditions	Yield
In i-Amyl alcohol Product distribution; Heating;
In i-Amyl alcohol

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + sodium thiophenolate (930-69-8) → nitro-2 dimethylsulfamoyl-4 diphenylsulfure (83472-52-0)

Conditions	Yield
In N,N-dimethyl-formamide for 5h; Heating;

4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) + 3-dimethylaminopropiononitrile (1738-25-6) → N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide (81676-66-6) + hydrochloride of 3-dimethylaminopropionitrile (18076-02-3) + acrylonitrile (107-13-1)

Conditions	Yield
In i-Amyl alcohol

1,1-Dimethylurea (598-94-7) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide (81676-66-6)

Conditions	Yield
at 200℃;

N-(p-ethoxyphenyl)urea (150-69-6) + 4-chloro-N,N-dimethyl-3-nitrobenzenesulfonamide (137-47-3) → 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide (67338-59-4)

Conditions	Yield
at 200℃;

Upstream product

• 60-29-7 diethyl ether 
• 15945-25-2 2-chloro-3-nitrobenzenesulfonyl chloride 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 97-08-5 3-nitro-4-chlorosulfonyl chloride 
• 506-59-2 N,N-dimethylammonium chloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 25678-54-0 Dibenzyl-dithiocarbamic acid 4-dimethylsulfamoyl-2-nitro-phenyl ester 
• 67338-59-4 3-nitro-4-p-phenetidino-benzenesulfonic acid dimethylamide 
• 118938-18-4 5-t-butyl-2-(4-dimethylsulfamoyl-2-nitrophenyl)-4-isoxazolin-3-one 
• 862298-40-6 4-[(2,2-dimethyl-4-oxo-4H-1,3-benzodioxin-5-yl)oxy]-N, N-dimethyl-3-nitrobenzenesulfonamide 
• 57824-29-0 1-amino-2-nitrobenzene-4-sulphonic acid dimethylamide 
• 83465-21-8 N-(dimethylamino-2 propyl) amino-2 dimethylsulfamoyl-4 diphenylsulfure 
• 83472-53-1 amino-2 dimethylsulfamoyl-4 diphenylsulfure 
• 99363-02-7 4-methoxy-N,N-dimethyl-3-nitrobenzenesulfonamide 
• 68528-28-9 3-Nitro-4-methylamino-benzolsulfonsaeure-dimethylamid 
• 93898-75-0 4-p-anisidino-3-nitro-benzenesulfonic acid dimethylamide 
• 81676-66-6 N,N-dimethyl-4-dimethylamino-3-nitrobenzenesulfonamide 
• 18076-02-3 hydrochloride of 3-dimethylaminopropionitrile 
• 107-13-1 acrylonitrile 
• 81676-81-5 2-nitro-4-dimethylsulfamoyl-N-ethylaniline 

Relevant articles and documents

Controlled synthesis of N, N-dimethylarylsulfonamide derivatives as nematicidal agents

Gramine can be intelligently and efficiently supplied with N, N-dimethylamino group and then reacted with the corresponding sulfonyl chlorides to synthesize N, N-dimethylarylsulfonamides. We herein designed and controlled synthesis of N, N-dimethylarylsulfonamide derivatives, and first reported the results of the nematicidal activity of 15 title compounds 3a-o against Meloidogyne incongnita in vitro, respectively. Among all of the title derivatives, compounds 3a, 3c, 3k, and 3o exhibited potent nematicidal activity with median lethal concentration (LC50) values ranging from 0.22 to 0.26 mg/L. Most noteworthy, N, N-dimethyl-4-methoxyphenylsulfonamide (3c) and N, N-dimethyl-8-quinolinesulfonamide (3o) showed the best promising and pronounced nematicidal activity, with LC50 values of 0.2381 and 0.2259 mg/L, respectively.

Preparation method of N,N-dimethylsulfamide derivatives

The invention discloses a preparation method of N,N-dimethylsulfamide derivatives and belongs to the technical field of synthesis of medical compounds. The preparation method comprises the following steps: reacting gramine, a reactant with sulfonyl chloride groups and an alkaline substance with any one of solvents such as CH2Cl2, CH3COCH3 and CH3CN at a temperature of minus 15 DEG C to 80 DEG C for 24-48 hours so as to obtain the product, wherein the molar ratio of the gramine to the reactant to the alkaline substance is (1.0-2.0):(1.2-4.0):(1.5-6.0). The N,N-dimethylsulfamide derivatives can be simply and efficiently prepared withlow cost, and the yield is up to 70-98%.

ARYLGLYCINE DERIVATIVES FOR USE AS GLYCINE TRANSPORT INHIBITORS

The present invention relates to compounds of Formula (I) and salts solvates and hydrates thereof. The invention further relates to pharmaceutical compositions containing said compounds and methods of treating neurological and neuropsychistric disorders using said compounds.

Tetrahydropyran derivatives

A novel tetrahydropyran derivative which has an excellent apo B-related lipoprotein secretion-inhibiting activity of the following general formula (I) or a salt thereof: R8 and R9 are the same or different and each represents H, lower alkyl, R30-lower alkyl-, R31R32N-, optionally- substituted hetero ring, or R33R34R35C-; R8 and R9 may together form optionally-substituted hetero ring-; R30 represents optionally-substituted aryl, optionally-substituted hetero ring-, or lower alkyl-O-; R31 represents optionally-substituted aryl, or optionally-substituted hetero ring-; R33 represents HO-lower alkyl-, or optionally-substituted hetero ring-lower alkyl-; R34 represents optionally-substituted aryl-.

Heterocyclic compounds

The invention provides compounds of formula (I) having nematicidal, insecticidal, acaricidal and fungicidal properties, compositions comprising them and processes and intermediates for their preparation: STR1 wherein: X is oxygen or sulphur; n is 0, 1 or 2; R1, R2, R3, and R4 are as described in the specification.

Anti-inflammatory 1-[3-(dialkylamino)propyl]-2-acylaminobenzimidazoles and 2-acylamino-3-[3-(dialkylamino)-propyl]imidazo[4,5-b]pyridines

1-[3-(Dialkylamino)propyl]-2-acylaminobenzimidazoles and 2-acylamino-3-[3-(dialkylamino)propyl]imidazo[4,5-b]pyridines and salts thereof with pharmaceutically acceptable acids, a novel class of compounds useful in the treatment of inflammatory conditions. Alternate methods of preparation are provided and the primary synthetic route is described in detail.