Sodium hydride → HCID 22941145, compound

HRID 1602459Notes

Reaction equation

HRID 1602459 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×

Conditions

Temperature
37.5 °C

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. extractionthe mixture was extracted three times with ethyl acetate
  3. washwashed with H2O and brine
  4. dry with materialdried over K2CO3
  5. concentrationconcentrated in vacuo
  6. customto give a white wax (3.7 g, 100%)

Sources & evidence

ORD record
ord-c19a086888434cbd8a0f55d92856f2c4
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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