Water → 2-isopropyl-N,N-diethylbenzamide

HRID 1768691Notes

Reaction equation

HRID 1768691 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 102630762-isopropyl-N,N-diethylbenzamideYield 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 solution 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 solution 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-1c9a0dd83bf547ddb6e441adc7fa31e8
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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