Triphenylphosphine → Ethyl 3-(3-nitro-4-chlorobenzyl)-2,4-dioxoimidazolidine-1-acetate

HRID 1416394Notes

Reaction equation

HRID 1416394 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[N+:13]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:19]O)([O-:15])=[O:14].[O:25]=[C:26]1[NH:30][C:29](=[O:31])[CH2:28][N:27]1[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[N+:13]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=1[Cl:24])[CH2:19][N:30]1[C:29](=[O:31])[CH2:28][N:27]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:26]1=[O:25])([O-:15])=[O:14]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 919334-Chloro-3-nitrobenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10773885HCID 10773885, compound

Product 1

HCID 10665913Ethyl 3-(3-nitro-4-chlorobenzyl)-2,4-dioxoimidazolidine-1-acetateYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.2 mL of diethyl azodicarboxylate in 30 mL of tetrahydrofuran was added to a solution of 5.13 g of 3-nitro-4-chlorobenzyl alcohol, 4.70 g of ethyl 2,4-dioxoimidazolidine-1-acetate and 8.68 g of triphenylphosphine in 30 mL of tetrahydrofuran at 0° C. The reaction mixture was poured over water and the mixture was extracted with ethyl acetate several times. The extracts were combined, washed with a saturated saline solution, dried over sodium sulfate and concentrated. The concentrate was purified by a silica gel column and recrystallized from a mixed solvent of ethanol and water to give 7.01 g of ethyl 3-(3-nitro-4-chlorobenzyl)-2,4-dioxoimidazolidine-1-acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate several times
  2. washwashed with a saturated saline solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by a silica gel column
  6. customrecrystallized from a mixed solvent of ethanol and water

Sources & evidence

ORD record
ord-14355166395f48d798e9428008f3ddc8
Source dataset
uspto-grants-1999_06
Patent number
US05912261

Reaction notes

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