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Sodium Hydroxide → N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide

HRID 515149
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515149
[CH2:1]([S:3][C:4]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[CH3:19])[CH:10]=[C:9]([CH3:20])[C:5]=1[C:6]([NH2:8])=[O:7])[CH3:2].[OH-].[Na+].[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:8][C:6](=[O:7])[C:5]2[C:9]([CH3:20])=[CH:10][C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C@H:14]3[CH3:19])=[CH:12][C:4]=2[S:3][CH2:1][CH3:2])=[CH:26][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 866997262-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide

Produkt 1

HCID 72187840N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamideAusbeute 32,4 %

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-[(3R)-3-methyl-morpholin-4-yl]-benzamide (0.05 g, 0.17 mmol) in benzene-tetrahydrofuran (1:1) (2 ml) are added tetrabutylammonium hydrogensulfate (0.006 g, 0.017 mmol) and 50% sodium hydroxide solution (1.5 ml) at RT. 4-Chlorobenzyl bromide (0.038 g, 0.19 mmol) is added and the reaction mixture is slowly heated to 70° C. The reaction mixture is stirred at 70° C. for additional 45 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, 8% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-ethylsulfanyl-6-methyl-4-[(3R)-3-methyl-morpholin-4-yl]-benzamide (example 4) (0.023 g, 0.055 mmol, 32%). [M+H]+ 419.2.

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, 8% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7d9eac8bc356473ea788768dc132f382
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108936B2

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