Dimethylformamide → HCID 59244769, compound

HRID 912250Notes

Reaction equation

HRID 912250 reaction equation
[CH3:1]N(C=O)C.[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1.[H-].[Na+].CI>O>[Br:6][C:7]1[CH:8]=[C:9]([N:13]([CH3:1])[C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 12123N-(3-Bromophenyl)acetamideHCID 24758Sodium hydride

Product 1

HCID 59244769HCID 59244769, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a DMF solution (15 ml) of N-(3-bromo-phenyl)-acetamide (1.19 g) obtained in Step A, 60% oily sodium hydride (279 mg) was added, followed by stirring at room temperature for 10 minutes. To this, methyl iodide (434 μl) was added, followed by stirring at room temperature for 21 hours. To this, water (30 ml) was added, followed by extraction with ethyl acetate (30 ml×2), and the organic layer was dried over sodium sulfate. The sodium sulfate was filtered off, followed by purification by silica gel column chromatography (dichloromethane/methanol=200/1), to obtain the desired compound (1.20 g, 94%).

Workup

  1. stirringby stirring at room temperature for 21 hours
  2. extractionfollowed by extraction with ethyl acetate (30 ml×2)
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. filtrationThe sodium sulfate was filtered off
  5. customfollowed by purification by silica gel column chromatography (dichloromethane/methanol=200/1)

Sources & evidence

ORD record
ord-dda48dbea7d743c6b1506fd0214f322c
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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