Water → HCID 10220552, compound

HRID 2120249Notes

Reaction equation

HRID 2120249 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[OH:6][CH2:7][CH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][C:12](=[O:18])[NH:13]2.O>O1CCCC1.CN(C)C=O>[O:18]=[C:12]1[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7][O:6][C:4](=[O:5])[NH:3][CH2:1][CH3:2])[NH:13]1

Participants

6

Reactant 3

HCID 962WaterHCID 8022Ethyl isocyanateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 10220552HCID 10220552, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl isocyanate (0.633 mL, 8 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL) and dimethylforamide (2 mL) under nitrogen atmosphere. The mixture was heated at 80° C. for 48 hours. The reaction was cooled, poured into water (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate/hexane to give 158 mg (16%) of ethyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as a white powder.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-9f09a5a7fa294a6ea567425105134e62
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

Loading…