Imidazolidinediones

Chemical Name 1 -[ [ [5-(4-nitrophenyl)-2-furanyl] -methylene] amino] -2,4-imidazolidinedione sodium salt... 

Chemical Name 1-[[(5-nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione Common Name N-(5-nitro-2-furfurylidene)-1-aminohydantoin Structural Formula CB—H... 

Therapeutic Function Antiepileptic Chemical Name 5,5-diphenyl-2,4-imidazolidinedione Common Name Diphenylhydantoin Structural Formula h... 

Chemical Name 5-Phenyl-5-(2-thienvl)-2,4-imidazolidinedione monosodium salt Common Name -... 

CN 5,5-diphenyl-3-[(phosphonooxy)methyl]-2,4-imidazolidinedione disodium salt... 

C18H17N3O 83-17-0) see Metamizole sodium l-(benzylidenamino)-2,4-imidazolidinedione (CK1H9N3O2 2827-57-8) see Azimilide hydrochloride... 

C 4H gN404 37389-83-6) see Trimethoprim 5-[[3,5-diamino-4-(4-methoxyphenoxy)phenyl]methyl]-5-methyl-2,4-imidazolidinedione (C sH2oN404 5165-04-8) see Etiroxate... 

Diphenyl-2,4-imidazolidinedione, d756 Diphenyl ketone, b53 Diphenylmethanone, b53 1,1-Diphenylmethylamine, al59 Diphenyl oxide, d753... 

Synonyms AI3-23669 AIDS-30050 BRN 0146013 Caswell No. 306 CCRIS 5900 Dactin Daktin Dantochlor Dantoin DCA DCDMH DDH Dichlorantin l,3-Dichloro-5,5-dimethyl-2,4-imidazolidinedione Dichlorodimethylhydantoin EINECS 204-258-7 EPA pesticide chemical code 028501 Halane NCI-C03054 NSC 33307 NSC 38630 Omchlor Sulfochloranthine. 

HYDANTOIN AND ITS DERIVATIVES. Hydamoin is an accepted name Tor 2.4-imidazolidinedione. This ring system rarely occurs in nature, although some natural products with hydamoin substructures are known. A huge number of derivatives have been prepared-... 

Diphenyl-2,4-imidazolidinedione, d672 Diphenyl ketone, b53 Diphenyl oxide, d667 Diphenylphosphorochloridate, d662... 

The search for other amino acid-based catalysts for asymmetric hydrocyanation identified the imidazolidinedione (hydantoin) 3 [49] and the e-caprolactam 4 [21]. Ten different substituents on the imide nitrogen atom of 3 were examined in the preparation, from 3-phenoxybenzaldehyde, of (S)-2-hydroxy-2-(3-phenoxy-phenyl)acetonitrile, an important building block for optically active pyrethroid insecticides. The N-benzyl imide 3 finally proved best, affording the desired cyanohydrin almost quantitatively, albeit with only 37% enantiomeric excess [49]. Interestingly, the catalyst 3 is active only when dissolved homogeneously in the reaction medium (as opposed to the heterogeneous catalyst 1) [49]. With the lysine derivative 4 the cyanohydrin of cyclohexane carbaldehyde was obtained with an enantiomeric excess of 65% by use of acetone cyanohydrin as the cyanide source [21]. 

N—[2—(5,5-Diphenyl-2,4-imidazolidinedion-3-yl)ethyl]-7-acetoxy-1-napthalene sulfonamide This substituted sulfonamide has a molecular weight of 543 daltons, and in the positive LD mass spectrum two ions at m/z 566 and m/z 582, corresponding to attachment of sodium and potassium ions, respectively, were observed. No significant photodissociation pathway other than loss of the attached cation was seen for either of these two ions. In the negative ion LD mass spectrum, an ion at m/z 500 originating from loss of C HjO was observed. This ion photodissociated when irradiated by the (gated) cw laser to produce an ion at m/z 251 (see Figure 9) (Equation 6). 

High resolution mass analysis of the ion at m/z 251 indicated that it has the empirical formula C h N202 > and is thus the 5,5-diphenyl-2,4-imidazolidinedione anion, resulting from cleavage of the C-N bond next to the imidazole ring. 

Jenhi, A. Lavergne, J.-P. Rolland, M. Martinez, J. Hasnaoui, A. 2,5-Imidazolidinedione formation from seven-membered cyclodipeptide rearrangement. Synth. Commun. 2001, 32, 1707-1714. 

While stirring at room temperature, l-bromo-4-chlorobutane (100 g, 0.5832 mole, 3 eq.) is added in one portion. The mixture becomes exothermic reaching around 35°C in approximately 30 min. The near-solution is heated a t approximately 80°C by steam bath for 4 h, cooled and stirred for approximately 8 h at room temperature (30°C). The cloudy mixture is filtered, removing a small amount of insoluble solid. The filtrate is concentrated under reduced pressure to a semi-solid residue. This residue is triturated with H20 (400 ml), collected, recrystallized from acetonitrile, and then air-dried to give 43.1 g (0.1467 mole) of l-phenylmethyleneamino-3-(4-chlorobutyl)-2,4-imidazolidinedione. 

A mixture of l-phenylmethyleneamino-3-(4-chlorobutyl)-2,4-imidazolidinedione (43.1 g, 0.1467 mole), acetone (1200 ml) and sodium iodide (48.4 9, 0.3227 mole) is heated to reflux. Reflux is maintained for 5 h. The mixture is filtered, collecting the insoluble. The filtrate is recharged with sodium iodide (10.0 g) and reflux is resumed and is maintained for 15 h. After cooling to room temperature, the mixture is filtered, removing the insoluble NaCI (total recovery, 9.5 g, 110%). The filtrate is poured into H20 (2000 ml) while stirring. After stirring for 30 min, the solid is collected and air-dried to yield 51.5 g (0.1337 mole) of l-phenylmethyleneamino-3-(4-iodobutyl)-2,4-imidazolidinedione. 

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