951-13-3

Basic information

• Product Name: 5,5-dimethyl-3-(morpholin-4-ylmethyl)imidazolidine-2,4-dione
• Synonyms: 2,4-imidazolidinedione, 5,5-dimethyl-3-(4-morpholinylmethyl)-
• CAS NO: 951-13-3
• Molecular Formula: C₁₀H₁₇N₃O₃
• Molecular Weight: 227.2603
• Mol File: 951-13-3.mol

Chemical Properties

• Density: 1.199g/cm³
• Refractive Index: 1.509
• CAS DataBase Reference: 5,5-dimethyl-3-(morpholin-4-ylmethyl)imidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-3-(morpholin-4-ylmethyl)imidazolidine-2,4-dione(951-13-3)
• EPA Substance Registry System: 5,5-dimethyl-3-(morpholin-4-ylmethyl)imidazolidine-2,4-dione(951-13-3)

Safety Data

• Hazardous Substances Data: 951-13-3(Hazardous Substances Data)

Upstream product

• 110-91-8 morpholine 
• 50-00-0 formaldehyd 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 

Downstream Products

• 6851-81-6 1,5,5-trimethylhydantoin 
• 1026228-19-2 1-(4-Nitrophenethyl)-5,5-dimethylimidazolidine-2,4-dione 

Relevant articles and documents

Synthesis and serotonergic activity of a series of 2-(JV-benzyl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives: Novel antagonists for the vascular 5-HT1B-like receptors

The synthesis and vascular 5-HT,B-like receptor activity of a novel series of 2-(Ar-benzyl)carboxamido-5-substitutedA-4W-dimethyltryptamine derivatives is described. Modifications to the 5-ethylene linked heterocycle are explored. Compounds such as N-benzyl-5-[2-(phthalimido)ethyl]-3-[2-(dimethylamino)ethyl]-l//-indole-2- carboxamide 22 (pA'B = 7.33), tfie 2-aminobenzyl analogue 24 (pA1B = 7.19), which both contain a phthalimide group, and A-4-benzyl-S[2-(l-benzyl-2,5-dioxoimidazolidin-4-yl)ethyl]-3-[2-(dimethylamino) ethyl]-l//-indole-2-carboxamide 81 (pATB = 7.05), which incorporates an N-benzylhydantoin moiety, have good 5-HT1B-like affinity and indicate that there may be a hydrophobic binding pocket within the vascular 5-HT1B-like receptor previously not considered. Compounds including N-benzyl-3-[2-(dimethylamino)ethyl]-5-[2-(2,4-dioxo-l,3-thiazolidinyl)ethyl]-l// -indole-2-carboxamide 39 (pA1B = 7.35) and the dimethyl analogue 46 (pA1B = 7.48) which contain a 2,4-thiazolidinedione moiety have good vascular 5-HT1B-like receptor affinity and show that the sulfur atom is well tolerated. Compound 61 which includes a methylsulfonyl substituent on the 1-nitrogen of the hydantoin ring system has the highest recorded 5-HT1B-like affinity for this series (pA1B = 7.54) and it is proposed that this functional group can interact with a secondary hydrogen bonding region within the receptor. Compounds 22, 24,39,46,61 and 81 also exhibited good selectivity over the a,-adrenoceptors. The most selective compound from this series is 46 which contains a 5,5-dimethylthiazolidine-2,4-dione group and which is 66-fold selective over the a,-adrenoceptors. This finding is consistent with the previous discovery that 5,5-dimethyl substitution on the hydantoin group in a related series of compounds afforded superior selectivity for 5-HT1B-like receptors over a,-adrenoceptors and other 5-HT receptors, in particular 5-HT2A receptors, relative to unsubstituted hydantoin analogues. The selectivity of these compounds for the vascular 5-HT1B-like receptor is discussed. Structure-activity relationship indicated a significant steric requirement of the 5-HT1B-like receptor subtype. Potential modes of binding for several of the compounds to a vascular 5-HT1B-like receptor pharmacophore model are also proposed. The Royal Society of Chemistry 1999.

Ring-Transformation of Imidazolidine-2,4-diones ( = Hydantoins ) to 4H-Imidazoles in the Reaction with 3-(Dimethylamino)-2,2-dimethyl-2H-azirines

At ca. 70 deg C, 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and 5,5-disubstituted hydantoins 4 in MeCN or i-PrOH give 2-(1-aminoalkyl)-5-(dimethylamino)-4,4-dimethyl-4H-imidazoles 5 in good yield (Scheme 2).These products are decarboxylated 1:1 adducts of 1 and 4.A reaction mechanism is suggested in analogy to the previously reported reactions of 1 and NH-acidic heterocycles containing the CO-NH-CO-NH moiety (Scheme 5).The formation of ureas 6 and 7 can be rationalized by trapping the intermediate isocyanate F by an amine.No reaction is observed between 1 and 1,5,5- or 3,5,5-trisubstituted hydantoins in refluxing MeCN or i-PrOH, but an N-isopropylation of 1,5,5-trimethylhydantoin (8b) occurs in the presence of morpholine (Scheme 3).The reaction of the bis(azirine)dibromozink complex 11 and hydantoines 4 in refluxing MeCN yields zink complexes 12 of the corresponding 2-(1-aminoalkyl)-4H-imidazoles 5 (Scheme 4).

Photochemical Cyclisation of 3-N-(Dialkylaminomethyl)imidazole-2,4-diones to 1,3,7-Triazabicyclooctanes

Ultraviolet irradiation of N-3 Mannich bases derived from hydantoin or from 5,5-disubstituted hydantoins (imidazole-2,4-diones), provides an efficient route to 1,3,7-triazabicyclooctane derivatives by photocyclisation to the C-4 carbonyl group.