Hydrochloric Acid → 1-[(E)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]-3-methylurea

HRID 868592Notes

Reaction equation

HRID 868592 reaction equation
[CH:1]([N:4]([CH:19]([CH3:21])[CH3:20])[CH2:5][CH2:6][N:7]1[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[C:10](=O)[C:8]1=[O:9])([CH3:3])[CH3:2].[CH3:22][NH:23][C:24](=[O:27])[NH:25][NH2:26].Cl.C(=O)(O)[O-].[Na+]>O.C(O)C>[CH3:22][NH:23][C:24](=[O:27])[NH:25]/[N:26]=[C:10]1/[C:8](=[O:9])[N:7]([CH2:6][CH2:5][N:4]([CH:19]([CH3:21])[CH3:20])[CH:1]([CH3:3])[CH3:2])[C:17]2[C:12]/1=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 256005n-methylhydrazinecarboxamideHCID 516892Sodium BicarbonateHCID 13934409HCID 13934409, compound

Product 1

HCID 1784859471-[(E)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]-3-methylureaYield 61.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.00 g of 1-(2-diisopropylaminoethyl)-5-methylisatin and 0.34 g of 4-methylsemicarbazide in 15 ml of a mixture of ethanol and water (2:1) was added 3.8 ml of a 1N-hydrochloric acid. The mixture was stirred for 16 hours at room temperature. To the reaction mixture was added an aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to obtain 0.77 g of (E)-1-(2-diisopropylaminoethyl)-5-methylisatin 3-(4-methylsemicarbazone) having a melting point of 157.5°-158.5° C.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe chloroform layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-175587cf0d0d4bb58142fc32a646438f
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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