Water → HCID 86625495, compound

HRID 2263098Notes

Reaction equation

HRID 2263098 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20].O>CN(C)C(=O)C.O1CCCC1>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])[CH:3]=2)[NH:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 27732135-Amino-2-oxindole

Product 1

HCID 86625495HCID 86625495, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-amino-1,3-dihydro-2H-indol-2-one (1.00 g, 6.75 mmol) and pyridine (1.64 ml, 20.3 mmol) in N,N-dimethylacetamide (6 ml) and tetrahydrofuran (50 ml) was added 2,2,2-trichloroethyl chloroformate (1.40 ml, 10.2 mmol) with ice-cooling, the mixture was stirred for 1 hour with ice-cooling, the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain the desired product (1.90 g, 87.2%) as a solid.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-10a63d46cdcc4dff89abf793b4cfd19b
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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