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Sodium Hydroxide → N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

HRID 515145
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515145
[CH2:1]([S:3][C:4]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[C:9]([CH3:19])[C:5]=1[C:6]([NH2:8])=[O:7])[CH3:2].[OH-].[Na+].[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:8][C:6](=[O:7])[C:5]2[C:9]([CH3:19])=[CH:10][C:11]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:12][C:4]=2[S:3][CH2:1][CH3:2])=[CH:25][CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 866997242-Ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide

Produkt 1

HCID 72187838N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
Katalysator
HCID 22633675Benzene tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (synthesized according to the methods described in sections b) and c) of example 1) (0.20 g, 0.71 mmol) in benzene-tetrahydrofuran (1:1) (16 ml) are added tetrabutylammonium hydrogensulfate (0.024 g, 0.071 mmol) and 50% sodium hydroxide solution (6 ml) at RT. The reaction mixture is heated to 70° C. and 4-chlorobenzyl bromide (0.15 g, 0.71 mmol) is added. The reaction mixture is stirred at 70° C. for 20 min. After completion of the reaction (monitored by TLC), the organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 28% ethyl acetate/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-morpholin-4-yl-benzamide (example 2) (0.095 g, 0.24 mmol, 50%). [M+H]+ 405.1.

Aufarbeitung

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe organic layer is separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (2×20 ml)
  4. washThe organic layer is washed with water (20 ml), brine (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto get the crude product, which
  8. customis purified by column chromatography (silica gel, 28% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-107606548ba64aac916d03a7c23b8180
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108936B2

Notizen zur Reaktion

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