Phenyl isocyanate → Methyl 1-N-(phenyl)carbamoyl-5-chlorooxindole-3-carboxylate

HRID 4481Notes

Reaction equation

HRID 4481 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12]([O:14][CH3:15])=[O:13].[C:16]1([N:22]=[C:23]=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[C:16]1([NH:22][C:23]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[CH:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2=[O:11])=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 21282067methyl 5-chloro-2-oxo-2,3-dihydro-1H-indole-3-carboxylate

Product 1

HCID 14097011Methyl 1-N-(phenyl)carbamoyl-5-chlorooxindole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 6.0 g. (0.027 mole) of methyl 5-chlorooxindole-3-carboxylate in 200 ml. of toluene was added 5.25 ml. (0.048 mole) of phenylisocyanate and the resulting reaction mixture heated to reflux overnight. The reaction mixture was cooled and diluted with petroleum ether to give, after filtration and drying, 2.0 g. of the desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customto give
  5. filtrationafter filtration
  6. customdrying

Sources & evidence

ORD record
ord-bbeceddc0faf432ab9c414f3a0a0c3be
Source dataset
uspto-grants-1988_02
Patent number
US04725616

Reaction notes

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