460994-52-9

Basic information

• Product Name: N-(6-acetyl-1,3-benzodioxol-5-yl)-4-methylbenzenesulfonamide
• Synonyms: N-(6-acetyl-1,3-benzodioxol-5-yl)-4-methylbenzenesulfonamide
• CAS NO: 460994-52-9
• Molecular Formula: C₁₆H₁₅NO₅S
• Molecular Weight: 333.359
• Mol File: 460994-52-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(6-acetyl-1,3-benzodioxol-5-yl)-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(6-acetyl-1,3-benzodioxol-5-yl)-4-methylbenzenesulfonamide(460994-52-9)
• EPA Substance Registry System: N-(6-acetyl-1,3-benzodioxol-5-yl)-4-methylbenzenesulfonamide(460994-52-9)

Safety Data

• Hazardous Substances Data: 460994-52-9(Hazardous Substances Data)

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 98-59-9 p-toluenesulfonyl chloride 
• 28657-75-2 2-amino-4,5-methylenedioxy-acetophenone 

Downstream Products

• 28657-75-2 2-amino-4,5-methylenedioxy-acetophenone 
• 1315477-74-7 7-methyl-5-tosyl-5H-[1,3]dioxolo[ 4,5-f]indole-6-carbaldehyde 
• 1315477-52-1 2-(5-(tosylamino)benzo[d][1,3]dioxol-6-yl)but-3-yn-2-ol 
• 1334483-40-7 9-methyl-5-tosyl-6,7-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-b]azepine 
• 1334483-31-6 1-cyclopropyl-1-(6-(tosylamino)benzo[d][1,3]dioxol-5-yl)ethanol 
• 1178907-41-9 N-(6-(2-hydroxybut-3-en-2-yl)benzo[d][1,3]dioxol-5-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Diastereoselective synthesis of 2,4-substituted tetrahydroquinolines via hf(otf)4-catalyzed substitution/cyclization of 2-aminobenzyl alcohols with styrenes

An efficient and convenient stereoselective synthetic approach to 2,4-substituted 1,2,3,4-tetrahydroquinoline has been developed. This catalytic procedure involves a sequential reaction of 2-aminobenzyl alcohol with styrenes in the presence of Hf(OTf)4 ca

Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides

Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.

1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis

A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright

Cyclopropyl carbinol rearrangement for benzo-fused nitrogen ring synthesis

A synthetic method that relies on gold-catalysed cyclopropyl carbinol rearrangement of 2-tosylaminophenyl cyclopropylmethanols to prepare 2,3-dihydro-1H-benzo[b]azepines and 2-vinylindolines efficiently is reported. The reactions were shown to be chemoselective, with secondary and tertiary alcohol substrates exclusively providing benzo-fused five- and seven-membered ring products, respectively. The ring-forming process was also found to proceed in moderate to excellent yields under mild conditions only in the presence of the gold and silver catalyst combination. The mechanism is thought to involve activation of the alcohol by the (p-CF3C6H 4)3PAuCl/AgOTf (Tf=triflate) catalyst, resulting in ionization of the starting material. The tertiary carbocationic intermediate generated in situ in this manner then triggers ring-opening of the cyclopropane moiety and trapping by the tethered aniline group to give the 2,3-dihydro-1H-benzo[b]azepine. Cyclopropane ring fragmentation of the secondary carbocationic analogue, on the other hand, results in diene formation followed by subsequent intramolecular hydroamination to afford the 2-vinylindoline. Copyright

Gold-catalyzed cycloisomerizations of 1-(2-(Tosylamino)phenyl)prop-2-yn-1- ols to 1H-Indole-2-carbaldehydes and (E)-2-(Iodomethylene)Indolin-3-ols

A method to prepare lH-indole-2-carbaldehydes and (E)-2-(iodomethylene) indolin-3-ols by gold(I)-catalyzed cycloisomerization of l-(2-(tosylamino) phenyl)prop-2-yn-1-ols with N-iodosuccinimide (NIS) is reported. The reactions were shown to be operationally simplistic and proceed efficiently for a wide variety of substrates, affording the corresponding products in good to excellent yields (70-99%). The mechanism is suggested to involve activation of the alkyne moiety of the substrate by the gold(I) catalyst. This triggers intramolecular addition of the tethered aniline moiety to give a vinyl gold intermediate, which undergoes iododeauration with NIS to give the (E)-2-(iodomethylene)indolin-3-ol adduct. Subsequent 1,3-allylic alcohol isomerization (1,3-AAI) followed by formylation of this vinyl iodide intermediate then gives the 1H-indole-2-carbaldehyde.

One-pot synthesis of 2,3-disubstituted N-tosylindoles from o-acyl-N-tosylanilines

The reaction of oacyl-N-tosylanilines with lithium trimethylsilyldiazomethane followed by treatment with t-BuLi and then electrophiles gave 2,3-disubstituted N-tosylindoles in a one-pot process. Georg Thieme Verlag Stuttgart.

New synthesis of 3-substituted indoles using lithium trimethylsilyldiazomethane

Lithium trimethylsilyldiazomethane smoothly reacted with N-tosyl-o-acylanilines to give 3-substituted indoles in good to high yields.