Ethylenediamine → 5-(2-Imidazolidinylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 464409Notes

Reaction equation

HRID 464409 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].CS[C:7](SC)=[C:8]1[C:13](=[O:14])[O:12][C:11]([CH3:16])([CH3:15])[O:10][C:9]1=[O:17]>CO>[NH:3]1[CH2:2][CH2:1][NH:4][C:7]1=[C:8]1[C:9](=[O:17])[O:10][C:11]([CH3:15])([CH3:16])[O:12][C:13]1=[O:14]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 17451285-[Bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 8301505-(2-Imidazolidinylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,2-Ethanediamine (1.6 mL) was added under nitrogen to a solution of 5-[bis(methylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (6 g, 24 mmole, described in example 3) in dry methanol (45 mL). The mixture was stirred at 20°-22° C. for 18 hr. The resultant precipitate was collected and dissolved in 5% methanol in chloroform (v/v). The solution was filtered through silica gel. The filtrate was concentrated under reduced pressure. The residue was crystallized from methanol-diethyl ether to give 4.4 g of the title compound; mp 181°-182° C.; NMR (CDCl3) δ 1.65 (s, 6H), 3.8 (s, 4H), 8.25 (m, 2H); IR (CHCl3) 3350, 1690, 1660, 1645, 1590 cm-1 ; UVλmax (MeOH) 243 nm (ε 25,500).

Workup

  1. customThe resultant precipitate was collected
  2. dissolutiondissolved in 5% methanol in chloroform (v/v)
  3. filtrationThe solution was filtered through silica gel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was crystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-cb2e3c738ca949aeb688f462ccfe9a3a
Source dataset
uspto-grants-1985_10
Patent number
US04547516

Reaction notes

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