Acetone → HCID 86707247, compound

HRID 870293Notes

Reaction equation

HRID 870293 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)=O>O>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:16][C:8]2[NH:9][C:10]3[C:15]([C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 3175273-phenyl-oxindole

Product 1

HCID 86707247HCID 86707247, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3-Phenyloxindole (1.15 g), 4-methylbenzenesulfonyl chloride (1.06 g) and sodium carbonate (0.41 g) are introduced as initial charge in 5.5 ml of water and 11 ml of acetone and heated to 80° C. with stirring in a preheated oil bath. After 20 minutes, 5 ml of acetone and 1 ml of water are then added and the mixture is heated for a further 30 minutes. The hot solution is filtered, and the solid is washed with 20 ml of water/acetone (1:1) and methanol and dried in vacuo. This gives 0.59 g of product in an HPLC purity of 98% (29% of theory). A structural elucidation by NMR verifies that it is the O-sulfonylated product. A further 0.67 g of product in an HPLC purity of 40% can be isolated from the filtrate (13% of theory).

Workup

  1. temperaturethe mixture is heated for a further 30 minutes
  2. filtrationThe hot solution is filtered
  3. washthe solid is washed with 20 ml of water/acetone (1:1) and methanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-22016864e8524a9b8679bd435e7ad552
Source dataset
uspto-grants-2015_03
Patent number
US08969553B2

Reaction notes

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