Water → ST50668002

HRID 234495Notes

Reaction equation

HRID 234495 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:10]([N:12]([CH2:16][CH3:17])[C:13](Cl)=[O:14])[CH3:11].O.CCOC(C)=O>N1C=CC=CC=1>[CH2:10]([N:12]([CH2:16][CH3:17])[C:13]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 8857Ethyl AcetateHCID 10328Indoline

Product 1

HCID 2987329ST50668002

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 6 g of indoline in 10 ml of pyridine is cooled to 0° C., 6.4 ml of diethylcarbamoyl chloride are added dropwise and the mixture is stirred for 18 hours at RT. Water is added to the reaction mixture, extraction is carried out with AcOEt, the organic phase is washed with water and with a 5% solution of potassium hydrogensulfate and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM as the eluent to give 8 g of the expected product, which is used as such.

Workup

  1. washthe organic phase is washed with water and with a 5% solution of potassium hydrogensulfate
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is evaporated off under vacuum
  4. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-aa3c81db24384ac5970958029fc02e5c
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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