Hydrochloric Acid → 3-Methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde

HRID 2378719ノート

反応式

HRID 2378719 の反応式
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([O:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:8]([CH:10]=1)[NH2:9].[CH3:22][S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>ClCCl>[CH3:22][S:23]([NH:9][C:8]1[CH:10]=[C:4]([CH:5]=[CH:6][C:7]=1[O:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[CH:3]=[O:2])(=[O:25])=[O:24]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 231179015-Dimethoxymethyl-2-(2-morpholinoethoxy)aniline

生成物 1

HCID 231178953-Methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde収率 95%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-dimethoxymethyl-2-(2-morpholinoethoxy)aniline obtained in Step 3 (0.27 g, 0.91 mmol) in dichloromethane (2.00 mL) was added with methanesulfonyl chloride (0.11 mL, 1.42 mmol) and pyridine (0.50 mL, 6.18 mmol), followed by stirring at room temperature for 10 hours. The reaction mixture was added with hydrochloric acid (3 mol/L, 3.00 mL), was stirred at room temperature for 20 minutes, was neutralized with a saturated aqueous sodium hydrogencarbonate solution (50 ml) and was extracted with ethyl acetate (50 mL×3). The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. the crude product was purified by silica gel column chromatography (chloroform, then methanol/chloroform=1/6) to obtain 3-methanesulfonylamino-4-(2-morpholinoethoxy)benzaldehyde (0.28 g, 95%).

後処理

  1. stirringwas stirred at room temperature for 20 minutes
  2. extractionwas extracted with ethyl acetate (50 mL×3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe crude product was purified by silica gel column chromatography (chloroform

出典と根拠

ORDレコード
ord-11ad16615ad24fb1b995aeb88a331d3f
出典データセット
uspto-grants-2008_12
特許番号
US07470717B2

反応ノート

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