Iodoethane → HCID 15325842, compound

HRID 864724Notes

Reaction equation

HRID 864724 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.C1CCCCC1>[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

7

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 2

HCID 8028TetrahydrofuranSolvent3×HCID 8078CyclohexaneSolvent

Procedure

To a solution of 9.3 ml (0.058 mol) of tetramethylethylenediamine 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 cyclohexane. 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 (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-2d9b9f9ce1ea40eda9ecb1f751235f50
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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