Methyl iodide → HCID 18512356, compound

HRID 1370814Notes

Reaction equation

HRID 1370814 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH2:18][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:30]>CN(C)C=O>[CH2:20]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH2:18][O:19][CH3:30])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18511941HCID 18511941, compound

Product 1

HCID 18512356HCID 18512356, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 46B (0.12 g, 0.33 mmoles) in anhydrous N,N-dimethylformamide (1 mL) was treated with 60% sodium hydride (0.016 g, 0.40 mmoles). After stirring for 10 minutes at room temperature, the mixture was treated with iodomethane (0.031 mL, 0.50 mmoles) and allowed to stir overnight at room temperature. The reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate (3×). The ethyl acetate phases were combined, dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 363 (M+H)+.

Workup

  1. stirringto stir overnight at room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fccc987a9aa645d6947fe5a6652becfc
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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