Sodium hydride → HCID 22941145, compound

HRID 342099Notes

Reaction equation

HRID 342099 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][O:10][N:11]([CH3:25])[C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[C:20]2[CH2:21][CH2:22][O:23][C:19]=2[CH:18]=[CH:17][CH:16]=1.[NH4+].[Cl-]>CN(C=O)C>[CH3:9][O:10][N:11]([CH3:25])[C:12]([C@@H:13]1[CH2:2][C@H:14]1[C:15]1[C:20]2[CH2:21][CH2:22][O:23][C:19]=2[CH:18]=[CH:17][CH:16]=1)=[O:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86753519HCID 86753519, compound

Product 1

HCID 22941145HCID 22941145, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Trimethylsulfoxonium iodide (9.9 g, 45 mmol) was added in small portions to a suspension of sodium hydride (1.8 g, 45 mmol) in DMF (120 mL). After the foaming had subsided (10 min), a solution of (trans)-N-methoxy-N-methyl-3-(2,3-dihydrobenzofuran-4-yl)propenamide (3.5 g, 15 mmol) in DMF (60 mL) was added dropwise, with the temperature maintained between 35°-40° C. The mixture was stirred for 3 h at room temperature. Saturated NH4Cl (50 mL) was added dropwise and the mixture was extracted three times with ethyl acetate. The organic extracts were combined, washed with H2O and brine, dried over K2CO3, and concentrated in vacuo to give a white wax (3.7 g, 100%).

Workup

  1. custom(10 min)
  2. temperaturemaintained between 35°-40° C
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. washwashed with H2O and brine
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated in vacuo
  7. customto give a white wax (3.7 g, 100%)

Sources & evidence

ORD record
ord-77b1151bad6a435bbbfa1a78a47c33f4
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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