Dimethylformamide → HCID 9796803, compound

HRID 2120244Notes

Reaction equation

HRID 2120244 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10][CH2:11][CH2:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][C:16](=[O:22])[NH:17]2.CN(C)C=O.[OH-].[Na+]>O1CCCC1>[O:22]=[C:16]1[CH2:15][C:14]2[C:18](=[CH:19][CH:20]=[CH:21][C:13]=2[CH2:12][CH2:11][O:10][C:8](=[S:9])[NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7673Phenyl IsothiocyanateHCID 14798Sodium HydroxideHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9796803HCID 9796803, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl isothiocyanate (0.45 mL, 3.75 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (443 mg, 2.5 mmol) in tetrahydrofuran (5 mL). The mixture was stirred at room temperature for 20 hours and then 70° C. for 8 hours. One mL of dimethylforamide was added to the mixture to make it homogenous and the heating was continued for another 42 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 452 mg (58%) of phenyl-thiocarbamic acid O-[2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl]ester as a white solid.

Workup

  1. wait70° C. for 8 hours
  2. waitthe heating was continued for another 42 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted with ethyl acetate (200 mL)
  5. washThe organic layer was washed with 1 N hydrochloric acid (100 mL) and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from methanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-7b294b2c87884d48a0dee2bc27a83726
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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