853995-67-2

Basic information

• Product Name: methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dimethoxyanthranilate
• Synonyms: methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dimethoxyanthranilate
• CAS NO: 853995-67-2
• Molecular Weight: 346.815
• Mol File: 853995-67-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dimethoxyanthranilate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dimethoxyanthranilate(853995-67-2)
• EPA Substance Registry System: methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4,5-dimethoxyanthranilate(853995-67-2)

Safety Data

• Hazardous Substances Data: 853995-67-2(Hazardous Substances Data)

Upstream product

• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 

Relevant articles and documents

3,1-Benzoxazin-4-ones, 3,1-Benzothiazin-4-ones and N-Arylcyanothioformamides

Anthranilic acid and 4,5-dichloro-1,2,3-dithiazolium chloride 1 give the delicate dithiazoloimino carboxylic acid 8 which on mild thermolysis gives 2-cyano-3,1-benzoxazin-4-one 6 and with triphenylphosphine gives 2-cyano-3,1-benzothiazin-4-one 7, both quantitatively; in general N-aryliminodithiazoles 2 with triphenylphosphine give the corresponding cyanothioformanilides 3, providing a route to these compounds from anilines in two mild steps.

A short synthesis of quinazolinocarboline alkaloids rutaecarpine, hortiacine, euxylophoricine A and euxylophoricine D from methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates

Reactions of methyl N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)anthranilates with tryptamine at room temperature produced 2-cyano-3-[2-(indol-3-yl)ethyl]-4(3H)-quinazolinones, which underwent cyclization on heating with TFAA/HCl(g) to afford quinazolinocarboline alkaloids rutaecarpine (1a), hortiacine (1b), euxylophoricine A (1c) and euxylophoricine D (1d) in excellent yields.

1,2,3-Dithiazoles and new route to 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones and N-arylcyanothioformamides

Treatment of methyl anthranilate with 4,5-dichloro-1,2,3-dithiazolium chloride 3 in dichloromethane ar room temperature, followed by addition of pyridine, gave the amino derivative 7 (R = Me) as expected; anthranilic acid, however, gave 4-oxo-4H-3,1-benzoxazine-2-carbonitrile 5.If triphenylphosphine was added to the reaction mixture instead of pyridine, methyl anthranilate gave methyl N-(cyanothioformyl)anthranilate 12 (X = o-CO2Me) whilst anthranilic acid gave 4-oxo-4H-benzo-3,1-thiazine-2-carbonitrile 6.These differences are explained mechanistically.When anthranilic acid was treated with the dithiazolium chloride 3 without the addition of pyridine, the delicate imino derivative 4 of the free carboxylic acid could be isolated (60percent).This when heated in boiling toluene gave the benzoxazinone 5 quantitatively, and with triphenylphosphine at room temperature it gave the benzothiazinone 6 quantitatively.These reactions provide a good route to benzo substituted 2-cyanooxazinones and 2-cyanothiazinones from the corresponding anthranilic acids.With triphenylphosphine in dichloromethane at room temperature the imines 11 in general (i.e. without an o-CO2H group) gave the corresponding N-arylcyanothioformamides 12 in very high yields, thus providing a good route to these compounds in two mild steps from the corresponding anilines.