Iodoethane → HCID 178477483, compound

HRID 2227482Notes

Reaction equation

HRID 2227482 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH3:25])=[C:12]([NH:21][C:22]([NH2:24])=[S:23])[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26](I)[CH3:27]>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH3:25])=[C:12]([NH:21][C:22](=[NH:24])[S:23][CH2:26][CH3:27])[CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 18474011HCID 18474011, compound

Product 1

HCID 178477483HCID 178477483, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the compound (47 mg) obtained in Example 7e, ethyl iodide (0.026 ml) and acetonitrile (1 ml) was heated under reflux for 4 hours and then concentrated at reduced pressure. Saturated sodium hydrogencarbonate solution was added to the resulting residue and extraction with chloroform was conducted. The organic layer was dried with anhydrous magnesium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=15:1) to give the titled compound (yield, 95%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated at reduced pressure
  4. additionSaturated sodium hydrogencarbonate solution was added to the resulting residue and extraction with chloroform
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-b0d59290f8fe44aeaf58e9181b948e99
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

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