Potassium Carbonate → HCID 70295664, compound

HRID 1421853Notes

Reaction equation

HRID 1421853 reaction equation
[NH2:1]OS(C1C(C)=CC(C)=CC=1C)(=O)=O.[Cl:15][C:16]1[C:21]2[CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:23][O:24][C:20]=2[C:19]([N:31]2[C:36](=[O:37])[CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[NH:33][C:32]2=[O:42])=[C:18]([F:43])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Cl:15][C:16]1[C:21]2[CH:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:23][O:24][C:20]=2[C:19]([N:31]2[C:36](=[O:37])[CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[N:33]([NH2:1])[C:32]2=[O:42])=[C:18]([F:43])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 70299085HCID 70299085, compound

Product 1

HCID 70295664HCID 70295664, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Aminooxysulfonyl-2,4,6-trimethylbenzene (0.5 g, 0.002 mole) was added all at once to a stirred solution of 3-[4-chloro-6-fluoro-3-phenyl-1,2(2H)-benzisoxazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.8 g, 0.002 mole) and potassium carbonate (0.4 g, 0.003 mole) in THF (50 mL). Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time, the reaction mixture was filtered and the filtrate was concentrated to a residue. The residue was subjected to silica gel column chromatography using 4:1 hexane and ethyl acetate. The product-containing fractions were combined and concentrated, yielding 0.6 gram of Compound 34, m.p. 171-173° C. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. filtrationAfter this time, the reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to a residue
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eff9e4e29c3147d6a6a303ce577b25ba
Source dataset
uspto-grants-2000_06
Patent number
US06080702

Reaction notes

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