Pyridine → N-(3-Iodophenyl)-4-(tetradecyloxy)benzeneacetamide

HRID 653798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 653798
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH2:15]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](Cl)=[O:38])=[CH:32][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:37](=[O:38])[CH2:36][C:33]2[CH:34]=[CH:35][C:30]([O:29][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:31][CH:32]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 122713-IodoanilineHCID 10021844p-Tetradecyloxyphenylacetylchloride

Produkt 1

HCID 15030163N-(3-Iodophenyl)-4-(tetradecyloxy)benzeneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 14.29 g of m-iodoaniline and 15.52 g of pyridine in 150 ml of tetrahydrofuran is added at room temperature over 20 minutes a solution of p-tetradecyloxyphenylacetyl chloride in 150 ml of tetrahydrofuran. The mixture is stirred overnight and the solvent removed. The residue is partitioned between dilute hydrochloric acid and warm chloroform. The separated organic layer is washed with dilute hydrochloric acid, dried and evaporated to a residue which is crystallized from carbon tetrachloride:hexane to give 25.0 g of the desired product as a pink solid, m.p. 108°-110° C.

Aufarbeitung

  1. customthe solvent removed
  2. customThe residue is partitioned between dilute hydrochloric acid
  3. temperaturewarm chloroform
  4. washThe separated organic layer is washed with dilute hydrochloric acid
  5. customdried
  6. customevaporated to a residue which
  7. customis crystallized from carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-45e3ac6068d046cf946c154d362d6350
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128351

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