Dimethylformamide → HCID 13934422, compound

HRID 868561Notes

Reaction equation

HRID 868561 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].Cl.[CH:13]([N:16]([CH:21]([CH3:23])[CH3:22])[CH2:17][CH:18](Cl)C)([CH3:15])[CH3:14].[H-].[Na+].[CH3:26]N(C)C=O>>[CH:21]([N:16]([CH:13]([CH3:14])[CH3:15])[CH:17]([CH3:18])[CH2:26][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])([CH3:22])[CH3:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7054IsatinHCID 24758Sodium hydrideHCID 21287233HCID 21287233, compound

Product 1

HCID 13934422HCID 13934422, compound

Conditions

Temperature
90 °C

Procedure

To a solution of 4.16 g of isatin and 6.06 g of 2-diisopropylamino-1-methylethyl chloride hydrochloride in 80 ml of dry N,N-dimethylformamide was added 2.28 g of sodium hydride (60% dispersion in mineral oil) with stirring under ice-cooling. The mixture was stirred for 30 minutes at room temperature and heated at 90° C. for 15 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was triturated with hexane and the precipitates were collected by filtration. The crystals were recrystallized from benzene-hexane to obtain 4.48 g of 1-(2-diisopropylaminopropyl)isatin having a melting point of 111°-112° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 30 minutes at room temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe ethyl acetate layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with hexane
  10. filtrationthe precipitates were collected by filtration
  11. customThe crystals were recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-abaf776a70004b818e1ec7211956edf7
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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