Ethyl isocyanate → HCID 13565644, compound

HRID 1760917Notes

Reaction equation

HRID 1760917 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10]2>>[CH2:1]([NH:3][C:4]([N:12]1[C:13]2[C:9](=[CH:8][C:7]([Cl:6])=[CH:15][CH:14]=2)[CH2:10][C:11]1=[O:16])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 8022Ethyl isocyanateHCID 1528015-Chlorooxindole

Product 1

HCID 13565644HCID 13565644, compoundYield 90%

Conditions

Temperature
138 °C

Procedure

Ethyl isocyanate (71.37 ml, 2.5 eq) was added to a solution of 5-chlorooxindole (60.45 g, 1.0 eq) in 500 ml xylenes. The reaction mixture was heated under reflux for 2 hours (138° C.) and then cooled to room temperature and evaporated to dryness. Isopropyl ether (500 ml) was added to the reaction vessel and the mixture was heated to 60° C. and stirred about 2 hours before cooling overnight in an ice bath to promote crystallization of the product. The white crystalline product was collected by filtration, washed once with isopropyl ether and then dried under vacuum to afford 5-Chloro-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethylamide in 90% yield (78.0 g), mp 121-122° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled to room temperature
  3. customevaporated to dryness
  4. additionIsopropyl ether (500 ml) was added to the reaction vessel
  5. temperaturethe mixture was heated to 60° C.
  6. temperaturebefore cooling overnight in an ice bath
  7. customcrystallization of the product
  8. filtrationThe white crystalline product was collected by filtration
  9. washwashed once with isopropyl ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-16590978400f45f8a88008ed79b1cb52
Source dataset
uspto-grants-2005_01
Patent number
US06846818B2

Reaction notes

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