Potassium tert-butoxide → HCID 178498690, compound

HRID 1639777Notes

Reaction equation

HRID 1639777 reaction equation
C(S[N:6]=[N:7][C:8]1[C:9]([CH3:19])=[C:10]([C:15]([F:18])=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(C)(C)C.CC(C)([O-])C.[K+]>CS(C)=O.O>[F:18][C:15]1[CH:16]=[CH:17][C:8]2[C:9](=[CH:19][NH:6][N:7]=2)[C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59334531Methyl 3-[(tert-butylthio)diazenyl]-6-fluoro-2-methylbenzoate

Product 1

HCID 178498690HCID 178498690, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of a crudely purified product (18.5 g, 65.1 mmol) of methyl 3-[(tert-butylthio)diazenyl]-6-fluoro-2-methylbenzoate in dimethyl sulfoxide (200 mL) was added a solution of potassium tert-butoxide (10.6 g, 98.0 mmol) in dimethyl sulfoxide (125 mL) at room temperature, and the mixture was stirred for 12 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (3.20 g, yield 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-d94e5e979edb478583cce5b6762217a9
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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