Sodium Hydroxide → HCID 9820255, compound

HRID 2120247Notes

Reaction equation

HRID 2120247 reaction equation
[C:1]1([S:7]([N:10]=[C:11]=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH2:18][C:19](=[O:25])[NH:20]2.[OH-].[Na+]>O1CCCC1.CN(C)C=O.N1C=CC=CC=1>[O:25]=[C:19]1[CH2:18][C:17]2[C:21](=[CH:22][CH:23]=[CH:24][C:16]=2[CH2:15][CH2:14][O:13][C:11](=[O:12])[NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])[NH:20]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 76096Phenylsulphonyl isocyanateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9820255HCID 9820255, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Benzene sulfonyl isocyanate (1.07 mL, 8 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops) under nitrogen atmosphere. The mixture was heated at 80° C. for 15 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 discarded and the basic aqueous layer was acidified with 6 N hydrochloric acid (18 mL) followed by extraction into ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 390 mg (27%) of benzene sulfonyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as an off-white powder.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate (200 mL)
  3. extractionfollowed by extraction into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methanol/ethyl acetate/hexane

Sources & evidence

ORD record
ord-b44ac0472c744bc186cb3969c891a1ed
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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