Water → HCID 15491043, compound

HRID 2227543Notes

Reaction equation

HRID 2227543 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-42e6ad75fd9341c8a748bc5902d90a20
Source dataset
uspto-grants-2002_07
Patent number
US06414012B1

Reaction notes

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