Iodoethane → HCID 19373061, compound

HRID 1768707Notes

Reaction equation

HRID 1768707 reaction equation
CN(C)CCN(C)C.[Li][CH:10]([CH2:12][CH3:13])[CH3:11].[CH3:14][O:15][C:16]1C=C[C:19]([C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C(I)C>C1COCC1>[CH2:12]([C:10]1[CH:11]=[C:16]([O:15][CH3:14])[CH:17]=[CH:18][C:19]=1[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH3:13]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 231459N,N-Diethyl-para-anisamideHCID 178418400CID 53628100

Product 1

HCID 19373061HCID 19373061, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of tetramethylethylenediamine (50.3 mL) in THF (800 mL) at -78° C. was added sec-BuLi (308 mL, 1.08M), followed by 4-methoxy-N,N-diethylbenzamide, (62.2 g). The mixture was stirred at -78° C. for 70 minutes, then ethyliodide (26.63 g, 333 mmol) was added over 35 minutes. The reaction mixture was warmed to room temperature and stirred for 1.5 hours. The reaction mixture was quenched with saturated NH4Cl (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a kugelrohr distillation at 190°-210° C. under high vacuum to afford 58.1 g of 2-ethyl-4-methoxy-N,N-diethylbenzamide.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 1.5 hours
  3. customThe reaction mixture was quenched with saturated NH4Cl (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was purified by a kugelrohr distillation at 190°-210° C. under high vacuum

Sources & evidence

ORD record
ord-4dffb49e0d90417d9e60d1d5f1ef01e9
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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