Iodoethane → HCID 15325841, compound

HRID 864722Notes

Reaction equation

HRID 864722 reaction equation
CN(C)[CH2:3][CH2:4]N(C)C.[CH2:9]([C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])[CH3:10].C([Li])(CC)C.C(I)C>C1COCC1.C1CCCCC1.O>[CH:9]([C:11]1[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=1[C:13]([N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])=[O:14])([CH2:3][CH3:4])[CH3:10]

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 225866n,n,2-triethylbenzamideHCID 178418400CID 53628100

Product 1

HCID 15325841HCID 15325841, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4.74 ml (0.031 mol) of tetramethylethylenediamine in 300 ml of THF (passed through alumina prior to use) was added 5.8 g (0.03 mol) of 2-ethyl-N,N-diethylbenzamide. The solution was cooled to -78° C. and treated with 34.9 ml (0.031 mol) of a 0.9M solution of s-butyl lithium in cyclohexane. When addition was complete, the mixture was stirred for twenty minutes and then treated with a solution of 3.2 ml (0.04 mol) of ethyl iodide while maintaining the temperature at -78° C. The temperature was then allowed to rise to ambient temperature and the mixture stirred for about sixteen hours and then poured into water. The resulting oil was separated and chromatographed on silica gel, eluting with 10% ethyl acetate/hexane to give 2.86 g (43%) of 2-sec.-butyl-N,N-diethylbenzamide as a yellow oil.

Workup

  1. additionWhen addition
  2. temperaturewhile maintaining the temperature at -78° C
  3. customto rise to ambient temperature
  4. stirringthe mixture stirred for about sixteen hours
  5. customThe resulting oil was separated
  6. customchromatographed on silica gel
  7. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d32f5256e7f94b98bdf322b118222099
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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