68239-27-0

Usage

InChI:InChI=1/C8H8ClNO3/c9-5-6(8(12)7(5)11)10-1-3-13-4-2-10/h1-4H2

Upstream product

• 110-91-8 morpholine 
• 2892-63-9 3,4-Dichlorocyclobut-3-ene-1,2-dione 
• 13368-42-8 4-(trimethylsilyl)morpholine 
• 68239-28-1 3-Morpholino-2,4,4-trichlor-2-cyclobutenon 
• 89872-31-1 1,1,3-trichloro-2,4,4-trimorpholinobutadiene 
• 54153-95-6 di-morpholin-4-yl-cyclobutenedione 

Downstream Products

• 54153-95-6 di-morpholin-4-yl-cyclobutenedione 

Relevant academic research and scientific papers

Oxocarbons and Related Compounds, VIII. - Squaric Amide Chlorides: Simple Methods of their Preparation and Cyclization of Specially Substituted Representatives to Annulated Cyclobutenediones

Squaric dichloride (1c) reacts with a great number of secondary amines and with several primary amines to afford the squaric amide chlorides 4d-z.A further simple method for the preparation of 4a-d, aa-ac has been found in the reaction of 1c with an equimolar amount of the trimethylsilylamines 9a-ac.On using a twofold molar amount of 4-(trimethylsilyl)morpholine (9d), dimorpholinocyclobutenedione (11) has been obtained.Reaction of hexamethyldisilazane (12) with 1c affords 3-amino-4-chloro-3-cyclobutene-1,2-dione (14).The squaric amide chlorides 4m, u-w suffer intramolecular cyclization by the action of AlCl3 to give the annulated cyclobutenediones 17a-d.The analogous cyclization of 4z yields 18 which is characterized by an sevenmembered ring condensed with the cyclobutenedione unit.

MECHANISMS AND INTERMEDIATES FOR SQUARIC ACID SYNTHESIS FROM HEXACHLOROBUTADIENE AND MORPHOLINE

The mechanistic course of the 3-stage synthesis of squaric acid from hexachlorobutadiene and morpholine has been elucidated, and 5 novel intermediates isolated and characterized.