Methyl iodide → N-[2,6-Bis(1-methylethyl)phenyl]-N'-methyl-N'-(tetradecylsulfonyl)urea

HRID 1656471Notes

Reaction equation

HRID 1656471 reaction equation
CI.[CH3:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:7]=1[NH:15][C:16]([NH:18][S:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:21])=[O:20])=[O:17])[CH3:5].N12CCCN=C1CCCC[CH2:37]2>CC#N.CCOC(C)=O>[CH3:14][CH:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:4]([CH3:3])[CH3:5])[C:7]=1[NH:15][C:16]([N:18]([CH3:37])[S:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])(=[O:20])=[O:21])=[O:17])[CH3:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 19611841N-[2,6-Bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea

Product 1

HCID 19611835N-[2,6-Bis(1-methylethyl)phenyl]-N'-methyl-N'-(tetradecylsulfonyl)ureaYield 77.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

CH3I (0.15 mL, 2 3 mmoles) was added dropwise to a room temperature solution of N-[2,6-bis(1-methylethyl)phenyl]-N'-(tetradecylsulfonyl)urea (1.0 g, 2.08 mmoles) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0 34 mL, 2.3 mmoles), stirring in 10 mL of CH3CN. The solution was stirred overnight at room temperature, diluted with EtOAc, washed with 1M HCl, H2O, brine, and dried (MgSO4). Filtration and evaporation afforded an oil which was flash chromatographed (silica gel, 10:1 hexane-ethyl acetate) to provide 800 mg of a colorless oil.

Workup

  1. washwashed with 1M HCl, H2O, brine
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and evaporation
  4. customafforded an oil which
  5. customchromatographed (silica gel, 10:1 hexane-ethyl acetate)

Sources & evidence

ORD record
ord-27213e6332f14733ac7a470dc2fcfaf5
Source dataset
uspto-grants-1993_10
Patent number
US05254589

Reaction notes

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