3808-20-6

Basic information

• Product Name: N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide
• Synonyms: N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide;2-/2-(4-Toluenesulfonylamino)-phenyl/-4H-3,1-benzoxazinone-4 (Luminor yellow-green 540 T);Benzenesulfonamide, 4-methyl-N-2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl-;4-methyl-N-[2-(4-oxo-1,3-benzoxazin-2-yl)phenyl]benzenesulfonamide;N-[2-(4-keto-1,3-benzoxazin-2-yl)phenyl]-4-methyl-benzenesulfonamide;2-(2-Tosylaminophenyl)-4H-3,1-benzoxazin-4-one;2-/2-(4-ToluenesulfonylaMino)-phenyl/-4H-3,1-benzoxazin-4-one (LuMinor yellow-green 540 T)
• CAS NO: 3808-20-6
• Molecular Formula: C₂₁H₁₆N₂O₄S
• Molecular Weight: 392.42774
• EINECS: 223-277-1
• Mol File: 3808-20-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 221℃
• Boiling Point: 587 °C at 760 mmHg
• Flash Point: 308.8 °C
• Appearance: /
• Density: 1.35±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.24E-12mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide(3808-20-6)
• EPA Substance Registry System: N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide(3808-20-6)

Safety Data

• Hazardous Substances Data: 3808-20-6(Hazardous Substances Data)

Usage

General Description

N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide is a complex, organic chemical compound. It is built from a benzoxazin ring system, which includes both phenyl and p-toluenesulfonamide groups. This structure suggests that this chemical falls under the broader class of organic compounds known as benzoic acids and derivatives. These are compounds containing a phenoxy group connected to the C1 carbon atom of a benzene ring. The precise properties and applications of N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]-p-toluenesulphonamide are not commonly cited in mainstream scientific literature, suggesting that it may be a more specialized or less commonly-used substance.

InChI:InChI=1/C21H16N2O4S/c1-14-10-12-15(13-11-14)28(25,26)23-19-9-5-2-6-16(19)20-22-18-8-4-3-7-17(18)21(24)27-20/h2-13,23H,1H3

Synthetic route

2,1-benzisothiazolin-3(1H)-one (40352-87-2) + 3-tosyl-2,1-benzisothiazolin-3(1H)-one (91859-89-1) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
In pyridine for 2h; Ambient temperature;	95%

4-toluenesulfonyl azide (941-55-9) + 2-phenyl-4H-3,1-benzoxazin-4-one (1022-46-4) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane for 24h; Inert atmosphere; Reflux; chemoselective reaction;	82%

N-(2-formylphenyl)-2-(4-methylphenylsulfonamido)benzamide → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
With tert.-butylhydroperoxide; cobalt(II) chloride In acetonitrile for 8h; Reflux;	64%

anthranilic acid (118-92-3) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
With pyridine at 0 - 20℃;	55%

2,1-benzisothiazolin-3(1H)-one (40352-87-2) + p-toluenesulfonyl chloride (98-59-9) → 3-tosyl-2,1-benzisothiazolin-3(1H)-one (91859-89-1) + 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
In pyridine for 1.5h;	A 30% B 32%

anthranilic acid (118-92-3) + 2-(Toluene-4-sulfonylamino)-benzoyl chloride (42840-02-8) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
In pyridine

2,1-benzisothiazolin-3(1H)-one (40352-87-2) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / pyridine / 0.5 h 2: 95 percent / pyridine / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 30 percent / pyridine / 1.5 h 2: 95 percent / pyridine / 2 h / Ambient temperature View Scheme

p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / pyridine / 0.5 h 2: 95 percent / pyridine / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 30 percent / pyridine / 1.5 h 2: 95 percent / pyridine / 2 h / Ambient temperature View Scheme

anthranil (271-58-9) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere; Sealed tube 2: tert.-butylhydroperoxide; cobalt(II) chloride / acetonitrile / 8 h / Reflux View Scheme

2-nitro-benzaldehyde (552-89-6) → 4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: tin(II) chloride hydrate / ethyl acetate; methanol / 24 h / 20 °C / Inert atmosphere 2: silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere; Sealed tube 3: tert.-butylhydroperoxide; cobalt(II) chloride / acetonitrile / 8 h / Reflux View Scheme

4-methyl-N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide (3808-20-6) → 2-({2-[(4-methylbenzene)sulfonamido]benzene}amido)benzoic acid (35889-75-9)

Conditions	Yield
With water In pyridine for 1h; Heating;

Upstream product

• 118-92-3 anthranilic acid 
• 42840-02-8 2-(Toluene-4-sulfonylamino)-benzoyl chloride 
• 40352-87-2 2,1-benzisothiazolin-3(1H)-one 
• 91859-89-1 3-tosyl-2,1-benzisothiazolin-3(1H)-one 
• 98-59-9 p-toluenesulfonyl chloride 
• 941-55-9 4-toluenesulfonyl azide 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 
• 552-89-6 2-nitro-benzaldehyde 
• 271-58-9 anthranil 

Downstream Products

• 35889-75-9 2-({2-[(4-methylbenzene)sulfonamido]benzene}amido)benzoic acid 

Relevant articles and documents

Ruthenium catalyzed chemo and site-selective C-H amidation of oxobenzoxazine derivatives with sulfonyl azides

An efficient, novel and general protocol towards the synthesis of highly functionalized ortho-amido oxobenzoxazine frameworks via ruthenium catalyzed intermolecular C-H amidation using sulfonyl azides as amidation components has been successfully developed for the first time. The salient features of this strategy are high chemo and site-selectivity, a wide range of substrate scope with excellent yields and good functional group tolerance.

Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones

The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.