Water → HCID 70242352, compound

HRID 427993Notes

Reaction equation

HRID 427993 reaction equation
ClC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([O:14][CH3:15])[C:10]([NH:12][CH3:13])=[O:11].[CH3:16][C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[OH:25].[H-].[Na+].O.[CH3:29]N(C)C=O>>[CH3:15][O:14][C:9]([CH2:29][O:25][C:18]1[CH:19]=[C:20]([CH3:24])[CH:21]=[C:22]([CH3:23])[C:17]=1[CH3:16])([C:4]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]([NH:12][CH3:13])=[O:11]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 127692,3,5-TrimethylphenolHCID 24758Sodium hydrideHCID 70243626HCID 70243626, compound

Product 1

HCID 70242352HCID 70242352, compoundYield 50%

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloromethyl-α-methoxy-N-methyl-phenylacetamide (0.25 g, 1.1 mmol) and 2,3,5-trimethylphenol (0.18 g, 1.3 mmol) in N,N-dimethylformamide (3 ml) was stirred at 0° C., and 60% oily sodium hydride (0.08 g, 2.0 mmol) was added thereto. The mixture was stirred at 0° C. for 70 minutes and then at room temperature for 1 hour, and ice and water were added in this order. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7/3) to give the desired compound α-methoxy-N-methyl-(2,3,5-trimethylphenoxymethyl)phenylacetamide (0.17 g, 50%) as an oil.

Workup

  1. waitat room temperature for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-66664b1ab33b482a9fcc37ec43866fdf
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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