Iodoethane → HCID 15325841, compound

HRID 1768712Notes

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 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-589da28d602b429481aefa107db20c92
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05378720

Reaction notes

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