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

HRID 515156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515156
[CH2:1]([S:3]([C:6]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([CH3:21])[C:7]=1[C:8]([NH2:10])=[O:9])(=[O:5])=[O:4])[CH3:2].[OH-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>C1C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:10][C:8](=[O:9])[C:7]2[C:11]([CH3:21])=[CH:12][C:13]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:14][C:6]=2[S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:27][CH:26]=1

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 866997322-(Ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide

Produkt 1

HCID 72187844N-[(4-chlorophenyl)-methyl]-2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamideAusbeute 115 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 22633675Benzene tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution 2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide (0.27 g, 0.88 mmol) in benzene-tetrahydrofuran (1:1) (10 ml) are added tetrabutylammonium hydrogensulfate (0.03 g, 0.09 mmol) and 15% sodium hydroxide solution (8 ml) at RT. 4-Chlorobenzyl bromide (0.083 g, 0.40 mmol) in tetrahydrofuran (1.5 ml) is added and the reaction mixture is slowly heated to 70° C. The reaction mixture is stirred at 70° C. for additional 25 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, 15% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-(ethylsulfonyl)-6-methyl-4-morpholin-4-yl-benzamide (example 8) (0.20 g, 0.46 mmol, 74%). [M+H]+ 437.1.

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, 15% acetone/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d14e48719d6a4836a1af24a995cfe2ac
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108936B2

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