Methyl iodide → HCID 10836157, compound

HRID 1975758Notes

Reaction equation

HRID 1975758 reaction equation
N12CCCN=C1CCCC[CH2:2]2.[CH3:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[NH:24][C:25]([NH:27][S:28]([N:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])(=[O:30])=[O:29])=[O:26])[CH3:14].CI>C(#N)C>[CH3:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25](=[O:26])[N:27]([S:28]([N:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])(=[O:30])=[O:29])[CH3:2])[CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 9844519HCID 9844519, compound

Product 1

HCID 10836157HCID 10836157, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (1.6 mL, 10.7 mmol) was added dropwise to a solution of N-[2,6-bis(1-methylethyl)phenyl]-N'-[(dibutylamino)sulfonyl]urea (4.0 g, 9.7 mmol) and methyl iodide (1.52 g, 10.7 mmol) in 100 mL acetonitrile at -15° C. The resulting mixture was warmed to room temperature and stirred for 16 hours. Concentrated in vacuo and partitioned between 1N HCl and ethyl acetate. The organic layer was dried with MgSO4, filtered, and concentrated to give an orange oil. Chromatography gave the title compound as a clear oil; 1H NMR (DMSO-d6) θ 8.57 (s, 1H), 7.31-7.15 (m, 3H), 3.33-3.21 (m, 7H), 3.05 (heptet, 2H), 1.57-1.46 (m, 4H), 1.35-1.20 (m, 4H), 1.13 (d, 12H), 0.90 (t, 6H). ##STR14##

Workup

  1. concentrationConcentrated in vacuo
  2. custompartitioned between 1N HCl and ethyl acetate
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an orange oil

Sources & evidence

ORD record
ord-9546d98f73794d42982aa37e257246d3
Source dataset
uspto-grants-1994_02
Patent number
US05288757

Reaction notes

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