4-Toluenesulfonyl chloride → HCID 57799630, compound

HRID 2100753Notes

Reaction equation

HRID 2100753 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:21])[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[O:16][CH3:17])[CH2:12][C:11](=[N:18]O)[C:10]2=[O:20])=[O:6].C1(C)C=CC(S(Cl)(=O)=[O:29])=CC=1>O>[C:11]([CH2:12][C:13]1[C:9]([C:10]([OH:20])=[O:29])=[CH:8][C:7]([C:5]([N:4]([CH3:3])[CH3:21])=[O:6])=[C:15]([O:16][CH3:17])[CH:14]=1)#[N:18]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 76608766HCID 76608766, compound

Product 1

HCID 57799630HCID 57799630, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (1.6 g, 40.54 mmol) in H2O (30 ml) was added of 2-Hydroxyimino-6-methoxy-3-oxo-indan-5-carboxylic acid dimethylamide (2.8 g, 10.67 mmol). The mixture was heated at 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 the precipitate was collected and dried to give product (2.5 g, 89.28%). LC-MS: m/e 261 (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. customthe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-1b188bf0cba84642bf6881c0a01a12ba
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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