4-Toluenesulfonyl chloride → HCID 57799765, compound

HRID 2100758Notes

Reaction equation

HRID 2100758 reaction equation
[OH-].[Na+].O[N:4]=[C:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][C:9]([O:18][CH3:19])=[C:10]([C:15]([NH2:17])=[O:16])[CH:11]=2)[CH2:6]1.C1(C)C=CC(S(Cl)(=O)=[O:27])=CC=1>O>[C:5]([CH2:6][C:7]1[C:12]([C:13]([OH:14])=[O:27])=[CH:11][C:10]([C:15]([NH2:17])=[O:16])=[C:9]([O:18][CH3:19])[CH:8]=1)#[N:4]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 76608712HCID 76608712, compound

Product 1

HCID 57799765HCID 57799765, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of NaOH (0.97 g, 19.2 mmol) in H2O (20 ml) was added 2-Hydroxyimino-6-methoxy-3-oxo-indan-5-carboxylic acid amide (1.5 g, 6.4 mmol). The mixture was heated to 50° C. Then p-Toluenesulfonyl chloride (1.6 g, 8.32 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 as a solid (1.33 g, 89%). LC-MS: m/e 233 (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-dcd1192aa10b432b94de89291b4ed277
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…