Diethyl Ether → n-Ethyl-2-chloro-6-(1,1-dimethylethoxy)benzamide

HRID 1458068

Reaction equation

HRID 1458068 reaction equation
[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[CH3:2].CN(CCN(C)C)C.[Li]C(CC)C.[Mg+2].[Br-].[Br-].CCOCC.C(OO[O:44][C:45]([CH3:48])([CH3:47])[CH3:46])(=O)C1C=CC=CC=1>C1COCC1>[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[C:10]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[CH3:2]

Participants

8

Reactant 6

HCID 3283Diethyl EtherHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 82241Magnesium BromideHCID 3479622-chloro-N-ethylbenzamideHCID 21744378t-Butylperoxy benzoateHCID 178418400CID 53628100

Product 1

HCID 18630260n-Ethyl-2-chloro-6-(1,1-dimethylethoxy)benzamideYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example f (3.7 g, 20 mmol) and TMEDA (6.0 mL, 40 mmol) in anhydrous THF (100 mL) at -78° C. under nitrogen was added dropwise 1.3M s-BuLi (34 mL, 44 mmol). After 30 min MgBr2.Et2O (15.5 g, 60 mmol) was added, and the solution was warmed to ambient temperature, then cooled to -78° C. and stirred for 1 h. t-Butylperoxy benzoate (4.3 g, 22 mmol) was added, and the solution was warmed to -30° C. and worked up in the usual manner. Purification by HPLC with 3:17 ethyl acetate/hexanes gave 1.7 g of the desired compound as a white solid, a yield of 33%. m.p. 126°-127° C.

Workup

  1. temperaturecooled to -78° C.
  2. additionwas added
  3. temperaturethe solution was warmed to -30° C.
  4. customPurification by HPLC with 3:17 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-243d51c6edad4d91b6be552bd9514ecf
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Linked notes

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