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

HRID 868582Notes

Reaction equation

HRID 868582 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)[O-].[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 516892Sodium BicarbonateHCID 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 69.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 137 mg of 1-(2-diisopropylaminoethyl)isatin and 120 mg of 4-benzylsemicarbazide hydrochloride in 2 ml of a mixture of ethanol and water (2:1) was stirred for 11 hours at room temperature, and an aqueous sodium bicarbonate solution was added to the reaction mixture. The precipitates were collected by filtration, washed with water and recrystallized from aqueous ethanol to obtain 147 mg of (E)-1-(2-diisopropylaminoethyl)isatin 3-(4-benzylsemicarbazone). Chemical properties of the product were identical with those of the product obtained by Example 5.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water
  3. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-0109db04136548a09c6462324af5b9b0
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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