30879-82-4

Usage

InChI:InChI=1/C8H16N2O/c1-8(2)5-9(3)7(11)10(4)6-8/h5-6H2,1-4H3

Upstream product

• 201230-82-2 carbon monoxide 
• 31892-15-6 N,N'-dimethyl-2,2-dimethylpropane-1,3-diamine 
• 122688-11-3 N,N'-(2,2-dimethylpropane-1,3-diyl)diformamide 
• 14060-74-3 4-hydroxy-1,3,5,5-tetramethyl-tetrahydro-pyrimidin-2-one 

Relevant academic research and scientific papers

Catalytic oxidative carbonylation of primary and secondary diamines to cyclic ureas. Optimization and substituent studies

W(CO)6-catalyzed oxidative carbonylation of 1,3-propanediamine to the corresponding urea has been examined under a variety of conditions. Following optimization, the Thorpe-Ingold effect on ring closure was studied using 2,2-dialkyl-1,3-propanediamines. For the 2,2-dimethyl- and 2,2-dibutyl-1,3-propanediamines, the yields were increased significantly as compared to that of the unsubstituted case. The eight-membered cyclic urea 5-butyl-5-ethyl-1,3-diazepan-2-one (5f) was formed in 38% yield, while only trace amounts of the cyclic urea were produced from the parent 1,5-pentanediamine. In a study of secondary diamines, yields from the carbonylation of N,N′-dialkyl-2,2-dimethyl-1,3-propanediamines were lower than those obtained from the primary diamines. The main byproducts from secondary diamines were tetrahydropyrimidine derivatives formed from a competitive reaction of the substrate with the oxidant and base.

Reduction Of 4-Hydroxy(Alkoxy)Hexahydropyrimidine-2-Thiones And 1,2,3,6-tetrahydropyrimidine-2-Thiones, By The NaBH4-CF3COOH System. Synthesis Of Hexahydropyrimidine-2-Thiones

A convenient method for the synthesis of hexahydropyrimidine-2-thiones by the reduction of the readily accesible 4-hydroxy(alkoxy)hexahydropyrimidine-2-thiones and 1,2,3,6-tetrahydropyrimidine-2-thiones by the NaBH4-CF3COOH system was proposed.

Process for producing cyclic ureas

A process for producing a cyclic urea is provided. The process comprises reacting a diamine expressed by the formula (II) wherein R represents hydrogen atom or a lower alkyl group and R' represent dimethylene group, a lower alkyl group-substituted dimethylene group, trimethylene group, a lower alkyl group-substituted trimethylene group, tetramethylene group, a lower alkyl group-substituted tetramethylene group, but a case where R represents hydrogen atom and R' represent dimethylene group, a case where R represents hydrogen atom and R' represents a lower alkyl group-substituted dimethylene group and a case where R represent methyl group and R' represents dimethylene group are excluded, with phosgene in the presence of a dehydrochlorinating agent. In the process, the diamine is first converted to its hydrochloride, followed by reacting the hydrochloride with phosgene in water solvent while maintaining a pH of the reaction liquid in the range of 5.0 to 8.0 by said dehydrochlorinating agent to obtain a cyclic urea expressed by the formula (I) STR1 wherein R and R' are each as defined above.