4-Toluenesulfonyl chloride → HCID 57799575, compound

HRID 2100747Notes

Reaction equation

HRID 2100747 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[C:10](=[O:16])[C:9](=[N:17]O)[CH2:8]2.C1(C)C=CC(S(Cl)(=O)=[O:26])=CC=1>O>[C:9]([CH2:8][C:7]1[CH:6]=[C:5]([O:4][CH3:3])[CH:13]=[C:12]([O:14][CH3:15])[C:11]=1[C:10]([OH:16])=[O:26])#[N:17]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 73198280HCID 73198280, compound

Product 1

HCID 57799575HCID 57799575, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (3.4 g, 85 mmol) in H2O (50 ml) was added of 5,7-Dimethoxy-indan-1,2-dione 2-oxime (5.0 g, 22.6 mmol). The mixture was heated to 50° C. Then p-Toluenesulfonyl chloride (5.7 g, 30 mmol) was added in portions to the mixture. The mixture was heated at 80° C. for 15 min. After cooling carefully to room temperature, the precipitate (a little) was removed from the mixture. Mother liquid was acidified by concentrated HCl to PH=3-4 and precipitate was formed. The precipitate was collected and dried to give product (3.5 g, 70%). LC-MS: m/e 220 (M−1).

Workup

  1. temperatureThe mixture was heated at 80° C. for 15 min
  2. temperatureAfter cooling carefully to room temperature
  3. customthe precipitate (a little) was removed from the mixture
  4. customprecipitate was formed
  5. customThe precipitate was collected
  6. customdried

Sources & evidence

ORD record
ord-0307bd5245df45159efe6c3fc3f163eb
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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