Diisopropylethylamine → 1-(2-Fluoro-4-nitrophenyl)-4-imidazolidinone

HRID 1373164Notes

Reaction equation

HRID 1373164 reaction equation
[NH:1]1[CH2:5][C:4](=[O:6])[NH:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[N:1]1[CH2:5][C:4](=[O:6])[NH:3][CH2:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 15020634-Imidazolidinone

Product 1

HCID 210262191-(2-Fluoro-4-nitrophenyl)-4-imidazolidinoneYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-imidazolidinone (9.5 g, 110.5 mmol), 3,4-difluoro nitrobenzene (12.2 ml, 110.5 mmol) and diisopropyl ethylamine (28.6 ml, 165 mmol) in dry DMF (80 ml) was heated to 60° C. overnight under argon. The reaction mixture was allowed to cool to room temperature and ice pieces were added. The solid formed was filtered and washed with water. The solid was dried under air to yield the nitro compound (19.5 g, 78.5%) as yellow crystals.

Workup

  1. additionice pieces were added
  2. customThe solid formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customThe solid was dried under air

Sources & evidence

ORD record
ord-c5f741b1b7e34f718d8b3fb9c77e992b
Source dataset
uspto-grants-2007_01
Patent number
US07160912B2

Reaction notes

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