4-Toluenesulfonyl chloride → HCID 57799696, compound

HRID 2100730Notes

Reaction equation

HRID 2100730 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])[C:10](=[O:19])[C:9](=[N:20]O)[CH2:8]2.C1(C)C=CC(S(Cl)(=O)=[O:29])=CC=1>O>[C:9]([CH2:8][C:7]1[CH:6]=[C:5]([O:4][CH3:3])[C:13]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:12][C:11]=1[C:10]([OH:19])=[O:29])#[N:20]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 76608737HCID 76608737, compound

Product 1

HCID 57799696HCID 57799696, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (5.15 g, 129.2 mmol) in H2O (100 ml) was added 5-Methoxy-6-(2-methoxy-ethoxy)-indan-1,2-dione 2-oxime (9.0 g, 34 mmol), and the mixture was heated to 50° C. Then p-Toluenesulfonyl chloride (8.5 g, 44.2 mmol) was added in portions to the mixture, and the mixture was heated at 80° C. for 15 min. After cooling to room temperature, the precipitate (a little) was filtered. The filtrate was acidified by concentrated HCl to PH=3-4, and the precipitate was collected and dried to give product (4.0 g, 44.1%). LC-MS: m/e 265 (M−1).

Workup

  1. temperaturethe mixture was heated at 80° C. for 15 min
  2. temperatureAfter cooling to room temperature
  3. filtrationthe precipitate (a little) was filtered
  4. customthe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-d43ec3d492874ef1b16ce120ce685eb0
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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