Acetone → HCID 86707248, compound

HRID 870296Notes

Reaction equation

HRID 870296 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH:11]2[C:19]3[C:14](=[C:15]([F:20])[CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:21])[N:4]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].CC(C)=O>O>[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:21][C:12]2[NH:13][C:14]3[C:19]([C:11]=2[C:5]2[N:4]=[C:3]([O:2][CH3:1])[N:8]=[C:7]([O:9][CH3:10])[N:6]=2)=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 679824373-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoroindolin-2-one

Product 1

HCID 86707248HCID 86707248, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-7-fluoro-1,3-dihydro-2H-indol-2-one (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, with stirring, heated to 80° C. in a preheated oil bath. After 45 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 0.76 g of product in an HPLC purity of 97% (42% of theory). Structure elucidation by NMR verifies that it is the O-sulfonylated product. A further 0.41 g of product in an HPLC purity of 89% can be isolated from the filtrate (21% of theory).

Workup

  1. filtrationthe hot solution is filtered
  2. washthe solid is washed with 20 ml of water/acetone (1:1) and methanol
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9514c0896c644b0a98cd85a6e33c0b62
Source dataset
uspto-grants-2015_03
Patent number
US08969553B2

Reaction notes

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