Hydrochloric Acid → Ethyl 3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetate

HRID 1416392Notes

Reaction equation

HRID 1416392 reaction equation
[O:1]=[C:2]1[CH2:6][N:5]([CH2:7][C:8]([O-:10])=[O:9])[C:4](=[O:11])[NH:3]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[CH2:18]N1C(=O)C(=O)N(CC(O)=O)C1=C)([O-:14])=[O:13].[H-].[Na+].[N+]([C:39]1C=C(C=C[CH:46]=1)CBr)([O-])=O.Cl>CN(C)C=O>[N+:12]([C:15]1[CH:16]=[C:17]([CH:31]=[CH:32][CH:33]=1)[CH2:18][N:3]1[C:2](=[O:1])[CH2:6][N:5]([CH2:7][C:8]([O:10][CH2:39][CH3:46])=[O:9])[C:4]1=[O:11])([O-:14])=[O:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 7219893HCID 7219893, compoundHCID 10638264HCID 10638264, compound

Product 1

HCID 10782009Ethyl 3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 815 mg of the above-prepared dioxoimidazolidine-l-acetate product of paragraph (1) dissolved in 30 mL of dimethylformamide was dropped into a suspension of 221 mg of sodium hydride in 20 mL of dimethylformamide at not higher than 0° C. The mixture was stirred for one hour more at the same temperature condition and then a solution of 1.3 g of 3-nitrobenzyl bromide dissolved in 30 mL of dimethylformamide was dropped thereinto at 0° C. The reaction mixture was stirred for two hours and added to an ice-cooled 2N hydrochloric acid with vigorous stirring. The resulting reaction mixture was extracted with ethyl acetate several times and the combined extract was washed with a saturated physiological saline solution and concentrated to give a residue. This residue was purified by a silica gel column to give 1.32 g of ethyl 3-(3-nitrobenzyl)-2,4-dioxoimidazolidine-1-acetate.

Workup

  1. additionwas dropped
  2. customat 0° C
  3. stirringThe reaction mixture was stirred for two hours
  4. customThe resulting reaction mixture
  5. extractionwas extracted with ethyl acetate several times
  6. extractionthe combined extract
  7. washwas washed with a saturated physiological saline solution
  8. concentrationconcentrated
  9. customto give a residue
  10. customThis residue was purified by a silica gel column

Sources & evidence

ORD record
ord-5b7a3409749e4af78210f62215a0b331
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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