Iodoethane → HCID 15325842, compound

HRID 266448Notes

Reaction equation

HRID 266448 reaction equation
CN(C)[CH2:3][CH2:4]N(C)C.C([Li])(CC)C.[CH2:14]([C:17]1[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=1[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])[CH2:15][CH3:16].C(I)C>C1COCC1>[CH3:16][CH2:15][CH:14]([C:17]1[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=1[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11068228HCID 11068228, compoundHCID 178418400CID 53628100

Product 1

HCID 15325842HCID 15325842, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of 9.3 ml (0.058 mol) of tetramethyl-ethylenediamine in 340 ml of THF at -78° C was added 52 ml of a 1.1M solution (0.057 mol) of s-butyl lithium in THF. The solution was then treated with a solution of 11.37 g (0.052 mol) of 2-propyl-N,N-diethylbenzamide in 75 ml of THF at -78° C. and the solution stirred for fifteen minutes and then treated with a solution of 8.3 ml of (0.104 mol) of ethyl iodide in THF. The solution was stirred for an hour and a half at -78° C. and then quenched by the addition of saturated ammonium chloride added dropwise at -78° C. The mixture was then allowed to warm to ambient temperature, diluted with diethyl ether, washed first with dilute hydrochloric acid, then with water, then with saturated sodium bicarbonate, then with brine dried and taken to dryness to give 12.91 g of crude product which was chromatographed on silica gel, eluting with 10% ethyl acetate/hexane to give 3.23 g (25%) of 2-(3-pentyl)-N,N-diethylbenzamide as a yellow oil.

Workup

  1. stirringThe solution was stirred for an hour
  2. customa half at -78° C. and then quenched by the addition of saturated ammonium chloride
  3. additionadded dropwise at -78° C
  4. additiondiluted with diethyl ether
  5. washwashed first with dilute hydrochloric acid
  6. dry with materialwith water, then with saturated sodium bicarbonate, then with brine dried
  7. customto give 12.91 g of crude product which
  8. customwas chromatographed on silica gel
  9. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-136e7e482d9042979c3b6cabb1b4e4ef
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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