Dimethylformamide → HCID 20079565, compound

HRID 1654205Notes

Reaction equation

HRID 1654205 reaction equation
[CH3:1]N(C)C=O.[CH3:6][O:7][C:8]1[CH:22]=[CH:21][C:11]([CH2:12][S:13][CH2:14][CH2:15][C:16]2[NH:17][CH:18]=[CH:19][N:20]=2)=[CH:10][CH:9]=1.[H-].[Na+].CI>O>[CH3:1][N:20]1[CH:19]=[CH:18][N:17]=[C:16]1[CH2:15][CH2:14][S:13][CH2:12][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20079580HCID 20079580, compound

Product 1

HCID 20079565HCID 20079565, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide (15 ml) solution of 2-[2-(p-methoxybenzylthio)ethyl]imidazole (1.5 g) was added 60% sodium hydride (0.29 g) in mineral oil at 0° C. To the mixture was added, 15 minutes later, methyl iodide (0.41 ml) at -20° C., followed by stirring for 10 minutes. The reaction mixture was poured into water (60 ml), which was subjected to extraction with methylene chloride (20 ml×three times). The organic layer was washed with water (20 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was subjected to a silica gel chromatography (3 cm×15 cm), eluting with methanol-methylene chloride (5:95). The desired fraction was concentrated under reduced pressure to afford 1-methyl-2-[2-(p-methoxybenzylthio)ethyl]imidazole (1.6 g) as a colorless oily product.

Workup

  1. additionTo the mixture was added, 15 minutes later
  2. customat -20° C.
  3. extractionwas subjected to extraction with methylene chloride (20 ml×three times)
  4. washThe organic layer was washed with water (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with methanol-methylene chloride (5:95)
  8. concentrationThe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b8e2e6c96d874d82b96aed290a6fba61
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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