2-Dimethylaminopyridine → HCID 20342661, compound

HRID 2050349Notes

Reaction equation

HRID 2050349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([CH:13]([CH3:15])[CH3:14])[C:11](=[O:16])[O:10][C:9]2=O)=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[O:27]=[C:28]1[N:32](CO)[C:31](=[O:35])[CH2:30][N:29]1[CH2:36][C:37]#[CH:38]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:12]([CH:13]([CH3:14])[CH3:15])[C:11]([O:10][CH2:9][N:32]2[C:31](=[O:35])[CH2:30][N:29]([CH2:36][C:37]#[CH:38])[C:28]2=[O:27])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 117895972,4-Imidazolidinedione, 3-(hydroxymethyl)-1-(2-propynyl)-HCID 132294943-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione

Product 1

HCID 20342661HCID 20342661, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(4-chlorophenyl)-4-isopropyloxazolidine-2,5-dione (1.32 mmol) and dimethylaminopyridine in 5 ml of dry tetrahydrofuran is added a solution of (2,4-dioxo-1-propargyl-3-imidazolidinyl)methanol (1.26 mmol) in 3 ml of dry tetrahydrofuran. The reaction mixture is stirred for about 20 hours, under dry air, and then diluted with ether followed by washing with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride. After drying over calcium sulfate, solvent is evaporated. The crude product is chromatographed on a rotary chromatograph eluting with 15% ether/hexane to give (2,4-dioxo-1-propargyl-3-imidazolidinyl)methyl 2-(4-chlorophenylamino)-3-methylbutanoate.

Workup

  1. customunder dry air
  2. additiondiluted with ether
  3. washby washing with saturated aqueous sodium bicarbonate, water and saturated aqueous sodium chloride
  4. dry with materialAfter drying over calcium sulfate, solvent
  5. customis evaporated
  6. customThe crude product is chromatographed on a rotary chromatograph
  7. washeluting with 15% ether/hexane

Sources & evidence

ORD record
ord-cc6ec4a96f164068a70efbd2438114eb
Source dataset
uspto-grants-1980_04
Patent number
US04200758

Reaction notes

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