Sodium hydride → HCID 13934411, compound

HRID 868562Notes

Reaction equation

HRID 868562 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].Cl.[CH:14]([N:17]([CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19]Cl)([CH3:16])[CH3:15].[H-].[Na+]>CN(C)C=O>[CH:14]([N:17]([CH:21]([CH3:23])[CH3:22])[CH2:18][CH2:19][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5](=[O:12])[C:6]1=[O:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 2365665-Fluoroisatin

Product 1

HCID 13934411HCID 13934411, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 3.30 g of 5-fluoroisatin and 4.00 g of 2-diisopropylaminoethyl chloride hydrochloride in 75 ml of dry N,N-dimethylformamide was added 1.60 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 then heated at 80° C. for 17 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with benzene, and the benzene layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-petroleum benzine (boiling point range of 50°-80° C., and containing 60-70% hexane; distributed by Wako Pure Chemical Industries, LTD) to obtain 4.97 g of 1-(2-diisopropylaminoethyl)-5-fluoroisatin having a melting point of 100°-102° 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 benzene
  6. washthe benzene layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from hexane-petroleum benzine (boiling point range of 50°-80° C., and containing 60-70% hexane; distributed by Wako Pure Chemical Industries, LTD)

Sources & evidence

ORD record
ord-e540a112f8334546ad4b19a398b2f0e2
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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