(NE)-N-(2,2-dimethylpropylidene)-2-methylpropane-2-sulfinamide → HCID 90204274, compound

HRID 1480245Notes

Reaction equation

HRID 1480245 reaction equation
Br[C:2]1[O:3][C:4]([CH3:7])=[N:5][N:6]=1.C([Mg]Cl)(C)C.[CH3:13][C:14]([CH3:24])([CH3:23])/[CH:15]=[N:16]/[S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18]>C1COCC1.C1(C)C=CC=CC=1>[CH3:13][C:14]([CH3:24])([CH3:23])[CH:15]([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:2]1[O:3][C:4]([CH3:7])=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 11506602(NE)-N-(2,2-dimethylpropylidene)-2-methylpropane-2-sulfinamideHCID 252195362-Bromo-5-methyl-1,3,4-oxadiazoleHCID 178418918HCID 178418918, compound

Product 1

HCID 90204274HCID 90204274, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of 2-bromo-5-methyl-1,3,4-oxadiazole (CAN 864750-58-3, 0.473 g, 2.91 mmol) in dry THF (8 ml) cooled down to −15° C. under an argon atmosphere was added isopropyl magnesium chloride, lithium chloride complex (2.23 ml, 2.91 mmol). (During the addition the temperature was kept below −12° C.). The reaction was then stirred at −15° C. for 30 minutes followed by slow addition of a solution of (NE)-N-(2,2-dimethylpropylidene)-2-methyl-propane-2-sulfinamide (CAN 917104-90-6, 500 mg, 2.64 mmol) in dry toluene (8 ml). The reaction was allowed to warm up to room temperature overnight. The reaction was quenched by addition of water. The reaction medium was diluted with ethylacetate and the organic phase was extracted with a saturated aqueous solution of ammonium chloride. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (462 mg, 64%). MS (ESI, m/z): 274.5 (M+H+).

Workup

  1. addition(During the addition the temperature
  2. customwas kept below −12° C.
  3. temperatureto warm up to room temperature overnight
  4. customThe reaction was quenched by addition of water
  5. additionThe reaction medium was diluted with ethylacetate
  6. extractionthe organic phase was extracted with a saturated aqueous solution of ammonium chloride
  7. customThe organic phase was collected
  8. extractionthe aqueous phase was back-extracted with ethylacetate
  9. dry with materialThe combined organic phases were dried over sodium sulfate
  10. customevaporated down to dryness
  11. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-5a5f5b25921e488aa6bdb5e8e5125bf3
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…