4-Toluenesulfonyl chloride → HCID 57799482, compound

HRID 2100740Notes

Reaction equation

HRID 2100740 reaction equation
[OH-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[C:13](=[O:22])[C:12](=[N:23]O)[CH2:11]2.C1(C)C=CC(S(Cl)(=O)=[O:32])=CC=1>O>[C:12]([CH2:11][C:10]1[CH:9]=[C:8]([O:7][CH2:6][CH2:5][O:4][CH3:3])[C:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:15][C:14]=1[C:13]([OH:22])=[O:32])#[N:23]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 76608725HCID 76608725, compound

Product 1

HCID 57799482HCID 57799482, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (0.55 g, 13.64 mmol) in H2O (10 ml) was added 5,6-Bis-(2-methoxy-ethoxy)-indan-1,2-dione 2-oxime (1.11 g, 3.59 mmol), and the mixture was heated to 50° C. Then p-Toluenesulfonyl chloride (0.89 g, 4.66 mmol) was added in portions to the mixture, and then the mixture was heated at 80° C. for 15 min. After cooling careful to room temperature, the precipitate (a little) was filtered off, the filtrate was acidified by concentrated HCl to PH=3-4. The precipitate was collected and dried to give product (0.777 mg, yield 70%). LC-MS: m/e 208 (M−1).

Workup

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

Sources & evidence

ORD record
ord-d330cba57f294f0e90d315c06304062a
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…