Methanesulfonamide → p-Hexadecylamino-N-(methylsulfonyl)benzamide

HRID 2163768

Reaktionsgleichung

Reaktionsgleichung von HRID 2163768
Cl.[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[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][CH2:16][CH3:17].[CH3:28][S:29]([NH2:32])(=[O:31])=[O:30]>N1C=CC=CC=1>[CH2:2]([NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:32][S:29]([CH3:28])(=[O:31])=[O:30])=[O:24])=[CH:21][CH:20]=1)[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][CH2:16][CH3:17]

Komponenten

4

Edukt 2

HCID 72879MethanesulfonamideHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Produkt 1

HCID 20437358p-Hexadecylamino-N-(methylsulfonyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 25.2 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride and 5.8 g. of methanesulfonamide in 250 ml. of pyridine was stirred under reflux for 2 hours and then concentrated in vacuo. The residue was partitioned between water and diethyl ether; the aqueous layer acidified with 1N HCl, and the organic layer separated, dried (MgSO4), and evaporated. Crystallization of the residual white solid from 60% aqueous acetic acid followed by CH2Cl2 -hexane afforded the product as a white solid.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and diethyl ether
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customCrystallization of the residual white solid from 60% aqueous acetic acid

Quellen und Nachweise

ORD-Eintrag
ord-afec514f980a49d1922885f242c417bd
Quelldatensatz
uspto-grants-1979_01
Patentnummer
US04136256

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