Water → HCID 10263076, compound

HRID 129034

Reaction equation

HRID 129034 reaction equation
C([Li])CCC.[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)([CH3:8])[CH3:7].[CH2:16]([N:18]([CH2:22][CH3:23])[C:19](Cl)=[O:20])[CH3:17].O>CCOCC>[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([N:18]([CH2:22][CH3:23])[CH2:16][CH3:17])=[O:20])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 23475o-BromocumeneHCID 178418339Butyllithium

Product 1

HCID 10263076HCID 10263076, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (2.5M, 100 mL) was added with stirring under nitrogen at 0°-5° C. during ten minutes to a solution of 2-isopropylbromobenzene in anhydrous ether (500 mL). The mixture was allowed to warm to room temperature, stirred at room temperature for six hours, and cooled to -60° C. A solution of diethylcarbamyl chloride (34 g) in anhydrous ether (50 mL) was added during 20 minutes while maintaining the temperature below -50° C. The temperature was allowed to rise to room temperature during one hour. Water (100 mL) was added. The ether layer was washed with saturated aqueous sodium chloride (200 mL), dried over magnesium sulfate and stripped of ether. Distillation of the residue (80°-90° C./0.1 mm Hg) gave 2-isopropyl-N,N-diethylbenzamide (44 g, 80% yield).

Workup

  1. temperaturecooled to -60° C
  2. temperaturewhile maintaining the temperature below -50° C
  3. waitto rise to room temperature during one hour
  4. washThe ether layer was washed with saturated aqueous sodium chloride (200 mL)
  5. dry with materialdried over magnesium sulfate
  6. distillationDistillation of the residue (80°-90° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-f791e72d887c4a629510bfe1bcab36b4
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Linked notes

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