Sodium Thiosulfate → HCID 90047349, compound

HRID 1507560Notes

Reaction equation

HRID 1507560 reaction equation
[F:1][C:2]1[C:3]([Si](C)(C)C)=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8](=[O:12])[C:7]2([CH3:14])[CH3:13].[I:19]Cl.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[F:1][C:2]1[C:3]([I:19])=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH3:11])[C:8](=[O:12])[C:7]2([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 90046406HCID 90046406, compound

Product 1

HCID 90047349HCID 90047349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-fluoro-1,3,3-trimethyl-6-(trimethylsilyl)indolin-2-one (9.9 g, 37.3 mmol) in dichloromethane (500 ml) at 0° C. was added iodine monochloride (37.3 ml, 37.3 mmol). The reaction mixture was warmed to room temperature and stirred for 16 hours. A saturated aqueous solution of sodium thiosulfate was added to the reaction mixture and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as off-white crystals (9.82 g).

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-885dffb7df454b93a87cef7ac9072069
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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