Ethanol → HCID 178457395, compound

HRID 868580Notes

Reaction equation

HRID 868580 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.[CH:22]1([NH:28][C:29](=[O:32])[NH:30][NH2:31])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(O)C.C([O-])(=O)C.[Na+]>O>[CH:22]1([NH:28][C:29](=[O:32])[NH:30]/[N:31]=[C:10]2/[C:8](=[O:9])[N:7]([CH2:6][CH2:5][N:4]([CH:18]([CH3:20])[CH3:19])[CH:1]([CH3:3])[CH3:2])[C:17]3[C:12]/2=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 12495002HCID 12495002, compoundHCID 139344081-(2-Diisopropylaminoethyl)isatin

Product 1

HCID 178457395HCID 178457395, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.91 g of 1-(2-diisopropylaminoethyl)isatin and 1.00 g of 4-cyclohexylsemicarbazide hydrochloride in 17 ml of a mixture of ethanol and water (2:1) was added 0.42 g of sodium acetate, and the mixture was stirred for 17 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and an aqueous sodium bicarbonate solution was added to the residue. The precipitates were collected by filtration, washed with water, and recrystallized from aqueous ethanol to obtain 0.99 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-(4-cyclohexylsemicarbazone) having a melting point of 164°-166° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionan aqueous sodium bicarbonate solution was added to the residue
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-1db09174fb94405d872004eaf6a60d77
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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