Iodoethane → HCID 15325841, compound

HRID 266447Notes

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

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 a solution of 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

additionWhen addition
temperaturewhile maintaining the temperature at -78 ° C
customto rise to ambient temperature
stirringthe mixture 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-d2c3045ee56f4f39abdbab18e209dc4b
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650422

Reaction notes

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