Water → isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester

HRID 2120260

Reaction equation

HRID 2120260 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15].O>O1CCCC1.CN(C)C=O>[O:13]=[C:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[CH2:3][CH2:2][O:1][C:18](=[O:19])[NH:17][CH:14]([CH3:16])[CH3:15])[NH:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 61277Isopropyl isocyanateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9903356isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl esterYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (3 g, 16.93 mmol) and isopropyl isocyanate (2.49 mL, 25.40 mmol) in tetrahydrofuran (16 mL) and dimethylformamide (6 mL) was heated at 80° C. for 64 hours. The reaction mixture was poured into water and extracted with ethyl acetate (400 mL), washed with brine, dried (sodium sulfate), and concentrated. The residue was recrystallized form methanol, ethyl acetate and hexanes to give 1.136 g (26%) of isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as crystalline solid.

Workup

  1. extractionextracted with ethyl acetate (400 mL)
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe residue was recrystallized form methanol, ethyl acetate and hexanes

Sources & evidence

ORD record
ord-9a2237619a824b71920dc83e5ba446ff
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Linked notes

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