Sodium hydride → HCID 86696500, compound

HRID 1615901Notes

Reaction equation

HRID 1615901 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])=[CH:12][CH:11]=1>CS(C)=O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[CH2:4][C@H:17]2[C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 21864661HCID 21864661, compound

Product 1

HCID 86696500HCID 86696500, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In a 1 L three neck flask, DMSO (100 mL) was rapidly stirred as 60% sodium hydride in mineral oil (4.59 g, 115 mmol) was added in 1.5 g portions. After the foaming subsided, trimethylsulfoxonium iodide (25.2 g, 115 mmol) was added portion wise over a 1 h period, maintaining the temperature below 35° C. The reaction was stirred at rt for 30 min. A soln of (E)-3-(4-fluorophenyl)-N-methoxy-N-methyl acrylamide (8 g, 38.2 mmol) in DMSO (50 mL) was then added dropwise maintaining the temperature below 35° C. After 45 min, the reaction was then slowly quenched with sat'd ammonium chloride (25 mL). The solution was then diluted with EtOAc. The solution was washed with water, dried with brine, dried over magnesium sulfate, and concentrated to give trans-2-(4-fluorophenyl)-N-methoxy-N-methylcyclopropanecarboxamide as a clear oil (8.1 g, 95%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.16-7.08 (m, 2H), 7.05-6.93 (m, 2H), 3.72 (s, 3H), 3.26 (s, 3H), 2.55-2.45 (m, 1H), 1.64 (ddd, J=9.2, 5.1, 4.3 Hz, 1H), 1.34-1.29 (m, 2H). LCMS: M+1=224.16.

Workup

  1. additionwas added in 1.5 g portions
  2. temperaturemaintaining the temperature below 35° C
  3. temperaturemaintaining the temperature below 35° C
  4. waitAfter 45 min
  5. customthe reaction was then slowly quenched with sat'd ammonium chloride (25 mL)
  6. additionThe solution was then diluted with EtOAc
  7. washThe solution was washed with water
  8. dry with materialdried with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c68575b02308461781fcd8bedda1ea70
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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