Ethanol → HCID 178457379, compound

HRID 868577Notes

Reaction equation

HRID 868577 reaction equation
[CH:1]([N:4]([CH:18]([CH3:20])[CH3:19])[CH2:5][CH2:6][N:7]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10](=O)[C:8]1=[O:9])([CH3:3])[CH3:2].Cl.[NH2:22][NH:23][C:24]([NH2:26])=[O:25].C([O-])(=O)C.[Na+].C(O)C>O>[CH:1]([N:4]([CH:18]([CH3:20])[CH3:19])[CH2:5][CH2:6][N:7]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)/[C:10](=[N:22]\[NH:23][C:24]([NH2:26])=[O:25])/[C:8]1=[O:9])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 139344081-(2-Diisopropylaminoethyl)isatin

Product 1

HCID 178457379HCID 178457379, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.3 g of 1-(2-diisopropylaminoethyl)isatin, 5.1 g of semicarbazide hydrochloride and 3.7 g of sodium acetate in 150 ml of a mixture of ethanol and water (2:1) was stirred for 17 hours at room temperature. The yellow precipitates were collected by filtration and washed with aqueous ethanol. The filtrate and the washed the aqueous ethanol solution were combined and concentrated under reduced pressure. An aqueous sodium bicarbonate solution was added to the residue. The yellow precipitates were collected by filtration and washed with dichloromethane. The yellow precipitates were combined and recrystallized from aqueous methanol to obtain 9.3 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-semicarbazone having a melting point of 193°-196° C.

Workup

  1. customThe yellow precipitates
  2. filtrationwere collected by filtration
  3. washwashed with aqueous ethanol
  4. washThe filtrate and the washed the aqueous ethanol solution
  5. concentrationconcentrated under reduced pressure
  6. additionAn aqueous sodium bicarbonate solution was added to the residue
  7. customThe yellow precipitates
  8. filtrationwere collected by filtration
  9. washwashed with dichloromethane
  10. customThe yellow precipitates
  11. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-ec24de67aa8f4af0b27b0e60d54ec68b
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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