Water → HCID 15469857, compound

HRID 883657Notes

Reaction equation

HRID 883657 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])[CH2:5]2.C(N([CH2:17][CH3:18])CC)C.Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].[OH2:30]>C1COCC1>[CH2:23]([O:22][C:20]([O:11][C:6]1[N:7]([C:20]([O:22][CH2:23][C:18]2[CH:17]=[CH:26][CH:25]=[CH:24][CH:29]=2)=[O:30])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1528015-Chlorooxindole

Product 1

HCID 15469857HCID 15469857, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 5-chlorooxindole (16.75 g; 100 mmol) and triethylamine (30.50 ml; 220 mmol) in THF (360 ml) was added dropwise benzyl chloroformate (37.9 ml; 240 mmol). After stirring at room temperature for 6 h, water was added and the organic phase was separated, washed again with brine, dried (MgSO4) and removed in vacuo to give a solid residue which was purified by recrystallisation (ethyl acetate), to give the title compound in 61% yield (HPLC purity 89%).

Workup

  1. customthe organic phase was separated
  2. washwashed again with brine
  3. dry with materialdried (MgSO4)
  4. customremoved in vacuo
  5. customto give a solid residue which
  6. customwas purified by recrystallisation (ethyl acetate)

Sources & evidence

ORD record
ord-062d8342bdd84bc1ba3e7063e7f92038
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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