Methyl iodide → HCID 59198692, compound

HRID 2068977Notes

Reaction equation

HRID 2068977 reaction equation
[CH:1]1([C:7]2[N:8]([C:12]3[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=3[N+:26]([O-:28])=[O:27])[C:15]([NH:17][CH2:18][CH2:19][O:20][CH2:21][CH3:22])=[O:16])[CH:9]=[CH:10][N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:31]I>CN(C)C(=O)C.O>[CH:1]1([C:7]2[N:8]([C:12]3[CH:13]=[C:14]([CH:23]=[CH:24][C:25]=3[N+:26]([O-:28])=[O:27])[C:15]([N:17]([CH2:18][CH2:19][O:20][CH2:21][CH3:22])[CH3:31])=[O:16])[CH:9]=[CH:10][N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59198602HCID 59198602, compound

Product 1

HCID 59198692HCID 59198692, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

To the solution of 3-(2-cyclohexyl-1H-imidazol-1-yl)-N-(2-ethoxyethyl)-4-nitrobenzamide as synthesized in above Production Example 48, 3.86 g in N,N-dimethylacetamide 32 mL, sodium hydride (formed by washing 60% sodium hydride, oiliness 600 mg with hexane) was added under cooling with ice. Then methyl iodide 1.55 mL was added and the ice bath was removed. After 1.8 hours' stirring, sodium hydride (formed by washing 60% sodium hydride, oiliness 200 mg with hexane) was added, followed by 5 hours' stirring. The reaction liquid was poured in water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. Distilling the solvent off, 3.35 g of the title compound was obtained.

Workup

  1. temperatureunder cooling with ice
  2. customthe ice bath was removed
  3. additionsodium hydride (formed by washing 60% sodium hydride, oiliness 200 mg with hexane) was added
  4. waitfollowed by 5 hours
  5. stirring' stirring
  6. customThe reaction liquid
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. distillationDistilling the solvent off, 3.35 g of the title compound
  11. customwas obtained

Sources & evidence

ORD record
ord-9da190f6d4e54d8b93cbbe25354a298b
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

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