Potassium Carbonate → HCID 22915169, compound

HRID 1377590Notes

Reaction equation

HRID 1377590 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[C:5]2[CH:8]=[C:9]([CH2:12]Br)[CH:10]=[CH:11][C:4]=2[S:3]1(=[O:15])=[O:14].[F:16][C:17]1[CH:18]=[C:19]([OH:30])[CH:20]=[C:21]([C:23]2([O:28][CH3:29])[CH2:27][O:26][CH2:25][CH2:24]2)[CH:22]=1.[C:31](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:16][C:17]1[CH:18]=[C:19]([CH:20]=[C:21]([C:23]2([O:28][CH3:29])[CH2:24][CH2:25][O:26][CH2:31][CH2:27]2)[CH:22]=1)[O:30][CH2:12][C:9]1[CH:10]=[CH:11][C:4]2[S:3](=[O:15])(=[O:14])[N:2]([CH3:1])[C:6](=[O:7])[C:5]=2[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22915172HCID 22915172, compoundHCID 22915173HCID 22915173, compound

Product 1

HCID 22915169HCID 22915169, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methyl-5-bromomethyl-1,1-dioxo-benzo[d]isothiazole-3-one (3.2 g), 4-(5-fluoro-3-hydroxyphenyl)-4-methoxytetrahydrofuran (2.4 g) and potassium carbonate (4.4 g) in 25 ml of dimethylformamide was stirred at room temperature for about 18 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate and evaporated. The residue was triturated with ether and filtered. The resulting solid was recrystallized from dichloromethane/ether to give 3 g of the title compound. m.p. 155°-156° C.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was triturated with ether
  6. filtrationfiltered
  7. customThe resulting solid was recrystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-35aac55780a24809887ed2435a43dc3e
Source dataset
uspto-grants-1997_09
Patent number
US05665749

Reaction notes

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