Water → HCID 15491043, compound

HRID 2296894Notes

Reaction equation

HRID 2296894 reaction equation
[NH2:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]([CH3:17])=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2.[CH2:19]([N:23]=[C:24]=[O:25])[CH2:20][CH2:21][CH3:22].O>C(Cl)(Cl)Cl>[CH2:19]([NH:23][C:24]([NH:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]([CH3:17])=[C:6]2[C:10]=1[N:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][CH2:7]2)=[O:25])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 8110Butyl isocyanateHCID 18388597HCID 18388597, compound

Product 1

HCID 15491043HCID 15491043, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-Amino-4,6-dimethyl-1-hexylindoline (800 mg) was dissolved in chloroform (20 ml) and butyl isocyanate (400 mg) was added, which was followed by stirring at room temperature for 18 hours. Water was added to the reaction mixture, and the mixture was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-50:1) and recrystallized from ethanol to give 450 mg of the title compound.

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-50:1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-191ed7bb4cd04cf8ba0c65cb05fd3a99
Source dataset
uspto-grants-2002_12
Patent number
US06489475B2

Reaction notes

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