Salicylamide → 5-Chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide hemihydrate

HRID 364360

Reaktionsgleichung

Reaktionsgleichung von HRID 364360
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[C:8]([C:9]([NH2:11])=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1.C(N)(=O)C1C(=CC=CC=1)O.Br[CH:25]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]1>CN(C)C=O.O>[OH2:10].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH:25]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH:25]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26]2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10]

Komponenten

7

Edukt 4

HCID 5147SalicylamideHCID 24758Sodium hydrideHCID 3480945-Chloro-2-hydroxybenzamideHCID 137262793-Bromo-1-methylpyrrolidine

Produkt 1

HCID 703936985-Chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide hemihydrateAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a cooled suspension of 2.4 g (0.41 mole) sodium hydride in 50 ml of dimethylformamide was added dropwise 17 g (0.1 mole) of 5-chlorosalicylamide dissolved in 50 ml of dimethylformamide at a rate such that the temperature did not exceed 20° C. After addition of the salicylamide was complete, 16.7 g (0.1 mole) of 3-bromo-1-methylpyrrolidine dissolved in 50 ml of dimethylformamide was added dropwise. The reaction mixture was stirred and heated at reflux for 19 hr. The cooled solution was diluted with 250 ml of water and extracted twice with 250 ml portions of chloroform. The chloroform was extracted thrice with 500 ml portions of 3N hydrochloric acid. The aqueous extracts were made alkaline with 50% sodium hydroxide and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate under reduced pressure gave 6 g (23%) of product as a beige solid. The solid was recrystallized from ethyl acetate, m.p. 126°-128° C.

Aufarbeitung

  1. customdid not exceed 20° C
  2. additionwas added dropwise
  3. temperatureheated
  4. temperatureat reflux for 19 hr
  5. extractionextracted twice with 250 ml portions of chloroform
  6. extractionThe chloroform was extracted thrice with 500 ml portions of 3N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. dry with materialDrying over magnesium sulfate and evaporation of the ethyl acetate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-13c4163777ba4598a61f7d24b074232b
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604388

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