Ethanol → 1-benzyl-3-[(E)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea

HRID 868581Notes

Reaction equation

HRID 868581 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.[CH2:22]([NH:29][C:30](=[O:33])[NH:31][NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)C.C([O-])(=O)C.[Na+]>O>[CH2:22]([NH:29][C:30](=[O:33])[NH:31]/[N:32]=[C:10]1/[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]2[C:12]/1=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 124017124-Benzylsemicarbazide hydrochlorideHCID 139344081-(2-Diisopropylaminoethyl)isatin

Product 1

HCID 1784573971-benzyl-3-[(E)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]ureaYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1.37 g of 1-(2-diisopropylaminoethyl)isatin and 1.20 g of 4-benzylsemicarbazide hydrochloride in 20 ml of a mixture of ethanol and water (2:1) was added 0.50 g of sodium acetate. The mixture was stirred for 18 hours at room temperature, and then concentrated under reduced pressure. 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 1.21 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-(4-benzylsemicarbazone) having a melting point of 164°-165° C.

Workup

  1. concentrationconcentrated 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-65eb94696a494d4da8d110106b4ca69d
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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