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

HRID 515156ノート

反応式

HRID 515156 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 8028Tetrahydrofuran溶媒HCID 22633675Benzene tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d14e48719d6a4836a1af24a995cfe2ac
出典データセット
uspto-grants-2015_08
特許番号
US09108936B2

反応ノート

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