Methyl iodide → HCID 58044231, compound

HRID 1918989Notes

Reaction equation

HRID 1918989 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:5]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:22]>C1COCC1>[CH3:22][N:11]([CH2:10][CH2:9][N:6]1[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]1)[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58044041HCID 58044041, compound

Product 1

HCID 58044231HCID 58044231, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 206c (5 g, 19.5 mmol) in THF (40 mL) was added NaH (938 mg, 23.4 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Iodomethane (1.7 mL, 25.4 mmol) was added and the mixture was stirred for additional 15 hours. It was then evaporated and purified by silical-gel column eluting with 2:1 petroleum ether/ethyl acetate to give 206d as a white solid (4.5 g, 85%). MS: (M+H)+ 271.

Workup

  1. stirringthe mixture was stirred for additional 15 hours
  2. customIt was then evaporated
  3. custompurified by silical-gel column
  4. washeluting with 2:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-46cf491302bd4c96850979bf2fabb0b5
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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