Iodoethane → HCID 15325841, compound

HRID 129055Notes

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])CCC.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

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-diethyl-benzamide. The solution was cooled to -78° C. and treated with 34.9 mL (0.031 mol) of a 0.9M solution of butyl lithium in cyclohexane. When addition was completed, the mixture was stirred for twenty minutes and then treated with a solution of 3.2 mL (0.04 mol) of ethyliodide while maintaining the temperature at -78° C. The temperature was then allowed to rise to ambient temperature and the mixture was 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

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

Sources & evidence

ORD record: ord-a8eeaab2a2ee4a0aa2b5451e2c95c529
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466701

Reaction notes

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