Diethyl Ether → HCID 53986966, compound

HRID 867474Notes

Reaction equation

HRID 867474 reaction equation
[Na].[O:2]=[C:3]1[NH:7][C:6](=[O:8])[CH:5](P(OCC)(=O)OCC)[NH:4]1.[N+:17]([C:20]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[CH:24][C:21]=1[CH:22]=O)([O-:19])=[O:18].C(OCC)C>C(O)C.C(Cl)(Cl)Cl>[N+:17]([C:20]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][S:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)(=[O:35])=[O:34])=[CH:24][C:21]=1[CH:22]=[C:5]1[NH:4][C:3](=[O:2])[NH:7][C:6]1=[O:8])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 3516088Diethyl 5-hydantoylphosphonateHCID 5360545SodiumHCID 15005593HCID 15005593, compound

Product 1

HCID 53986966HCID 53986966, compoundYield 8.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6212ChloroformSolvent

Procedure

Sodium (0.386 g, 0.017 g, atom) was dissolved in ethanol (70 mL) and diethyl 2,4-dioxoimidazolidine-5-phosphonate (3.96 g, 17 mmol) added. After 1 hour, a solution of 2-nitro-5-[4-(phenylsulfonyl)butoxy]benzaldehyde (4.70 g, 13 mmol) (prepared by alkylating 5-hydroxy-2-nitrobenzaldehyde with 4-phenylsulfonylbutyl bromide) in ethanol and chloroform was added. After 20 minutes, the solvent was evaporated and the residue extracted with chloroform to give a foamy solid which was dissolved in acetontirile. Diethyl ether was added to the point of precipitate nd the mixture allowed to stand overnight. A solid (0.86 g) was collected and further purified gy crystallication from acetonitrile-diethyl ether to give 5-[[2-nitro-5-[4-(phenylsulfonyl)butoxy]phenyl]methylene]-2,4-imidazolidinedione (0.5 g). Concentration of the combined mother liquors afforded 4.1 g of material that was used without further purification. Yield (4.6 g, 61%). Crystallized material had m.p. 150°-152° C.

Workup

  1. waitAfter 20 minutes
  2. customthe solvent was evaporated
  3. extractionthe residue extracted with chloroform
  4. customto give a foamy solid which
  5. dissolutionwas dissolved in acetontirile
  6. waitto stand overnight
  7. customA solid (0.86 g) was collected

Sources & evidence

ORD record
ord-dd09fade807c481ea144f6fc2edf3369
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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