1-Bromohexane → N-(4-Aminophenyl)-N-hexylacetamide

HRID 1983567

Reaktionsgleichung

Reaktionsgleichung von HRID 1983567
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:6]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7](=[O:9])[CH3:8])=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 312304-Aminoacetanilide

Produkt 1

HCID 57713043N-(4-Aminophenyl)-N-hexylacetamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4′-aminoacetanilide (1.00 g, 6.66 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% dispersion in mineral oil; 0.28 g, 7.0 mmol). After 5-10 minutes, 1-bromohexane was added dropwise to the mixture. The reaction was stirred for one hour and then partitioned between ethyl acetate and water. The organic layer was washed with additional water, dried (sodium sulfate) and concentrated. The resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol) to afford 1.32 g (84%) of product as a viscous amber oil: 1H NMR (CDCl3) δ 6.91 (d, J=8.7 Hz, 1H), 6.68 (d, J=8.7Hz, 1H), 3.78 (br s, 2H), 3.61 (t, J=7.9Hz, 2H), 1.81 (s, 3H), 1.33-1.18 (m, 2H), 1.17-1.08 (m, 6H), 0.85 (t, J=6.9 Hz, 3H) ppm.

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with additional water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-35b4111d6cad4ddbabfc43a67b491af2
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07541466B2

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