Acetic Acid → N-acetyl-N-2-octyl-4-iodoaniline

HRID 21430Notes

Reaction equation

HRID 21430 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])=[CH:4][CH:3]=1.[C:17](O)(=[O:19])[CH3:18].C(OC(=O)C)(=O)C>CCOCC>[C:17]([N:8]([CH:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH3:10])[C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 9927521N-(4'-iodophenyl)-2-aminooctane

Product 1

HCID 9907537N-acetyl-N-2-octyl-4-iodoanilineYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A flask containing N-(4'-iodophenyl)-2-amino octane (1.50 g, 4.5 mmol) was charged with acetic acid (15 ml) and acetic anhydride (15 ml). The reaction flask was immersed in an oil bath which was warmed to 70° C. over a period of 0.5 hr. After stirring for 19 hrs, the reaction was allowed to cool, diluted with ether (200 ml), washed with water (2×50 ml), saturated aqueous sodium bicarbonate (4×50 ml), water (2×50 ml) and brine (50 ml), dried (Na2SO4), filtered, and evaporated in vacuo. Flash column chromatography (silica, 1:4; EtOAc:hexanes) provided N-acetyl-N-2-octyl-4-iodoaniline (1.48 g, 70%) as a white solid. Mp 60°-62° C.

Workup

  1. customThe reaction flask was immersed in an oil bath
  2. temperatureto cool
  3. washwashed with water (2×50 ml), saturated aqueous sodium bicarbonate (4×50 ml), water (2×50 ml) and brine (50 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-729ea807b9614b928be9ddb5af805e35
Source dataset
uspto-grants-1995_06
Patent number
US05424056

Reaction notes

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