Iodoethane → 2-Chloro-N-(2-ethoxyethyl)-N-ethyl-6-(trimethylsilyl)benzamide

HRID 1440566Notes

Reaction equation

HRID 1440566 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:29])[C:18]1[C:23]([Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:28])[CH3:12].[CH2:30](I)[CH3:31]>C1COCC1>[Cl:28][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([Si:24]([CH3:27])([CH3:26])[CH3:25])[C:18]=1[C:17]([N:16]([CH2:15][CH2:14][O:13][CH2:11][CH3:12])[CH2:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 18630026N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide

Product 1

HCID 186302162-Chloro-N-(2-ethoxyethyl)-N-ethyl-6-(trimethylsilyl)benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1M THF solution of sodium bis(trimethylsilyl)-amide (7.7 mL, 7.7 mmol) was added dropwise over 5 min to a solution of N-(2-ethoxyethyl)-2-chloro-6-(trimethylsilyl)benzamide (2.1 g, 7 mmol) in THF (30 mL). The resulting mixture was stirred for 1 h at RT, then a solution of ethyl iodide (1.31 g, 8.4 mmol) in THF (15 mL) was added with a mild exotherm. The resulting reaction mixture was stirred overnight, then was partitioned between ethyl acetate and dilute aq citric acid. The ethyl acetate phase was washed with sat aq NaHCO3 followed with brine, then was dried (MgSO4) and concentrated to afford 1.9 g of the title compound as an amber oil, an 83% yield.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred overnight
  3. customwas partitioned between ethyl acetate and dilute aq citric acid
  4. washThe ethyl acetate phase was washed with sat aq NaHCO3
  5. dry with materialwas dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-37f780e7229149659b43659588ba286d
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

Loading…