Isoamylamine → 1-[(Z)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]-3-(3-methylbutyl)urea

HRID 868583Notes

Reaction equation

[CH:1]([N:4]([CH:22]([CH3:24])[CH3:23])[CH2:5][CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)/[C:10](=[N:17]\[NH:18][C:19]([NH2:21])=[O:20])/[C:8]1=[O:9])([CH3:3])[CH3:2].[CH2:25](N)[CH2:26][CH:27]([CH3:29])[CH3:28]>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:25]([NH:21][C:19](=[O:20])[NH:18]/[N:17]=[C:10]1\[C:8](=[O:9])[N:7]([CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:22]([CH3:24])[CH3:23])[C:16]2[C:11]\1=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:26][CH:27]([CH3:29])[CH3:28]

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 1.10 g of (E)-1-(2-diisopropylaminoethyl)isatin 3-semicarbazone and 0.29 g of isopentylamine in a mixture of 150 ml of dry toluene and 20 ml of dry N,N-dimethylformamide was stirred for 23 hours at 120° C. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane. The solution was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel flash column chromatography (eluent: chloroform) to obtain 1.12 g of (Z)-1-(2-diisopropylaminoethyl)isatin 3-(4-isopentylsemicarbazone) in a viscous oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in dichloromethane
washThe solution was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified with silica gel flash column chromatography (eluent: chloroform)

Sources & evidence

ORD record: ord-385e665f5b534bb88252c05acb5b8f6f
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04780477

Reaction notes

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