Dichloromethane → 2-[4-(Hexadecyloxy)phenoxy]-N-(2-pyridinylmethyl)acetamide

HRID 247996Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247996
[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24](Cl)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(Cl)Cl.[NH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([O:17][C:18]1[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24]([NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[O:25])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 195092-PyridinemethanamineHCID 516892Sodium BicarbonateHCID 104317244-Hexadecyloxyphenoxyacetic chloride

Produkt 1

HCID 190153632-[4-(Hexadecyloxy)phenoxy]-N-(2-pyridinylmethyl)acetamideAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. solution of 3.0 g of product from Example 87 is added 50 ml of methylene chloride, 0.829 g of 2-(aminomethyl)pyridine and 2.31 g of pyridine. The reaction is stirred at 0° C. for 3 hours; followed by 20 hours at room temperature. The mixture is poured into chloroform and saturated sodium bicarbonate. The aqueous layer is extracted with chloroform and the combined chloroform layers are washed with saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane) to give 2.90 g of the desired product as a colorless solid.

Aufarbeitung

  1. waitfollowed by 20 hours at room temperature
  2. extractionThe aqueous layer is extracted with chloroform
  3. washthe combined chloroform layers are washed with saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography (silica gel: 75% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cf18f3aceede499f952fb287d0362944
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208247

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