Hydrochloric Acid → 4-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-(2-(methylsulfinyl)ethoxy)benzamide

HRID 620262

反応式

HRID 620262 の反応式
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][S:22][CH3:23])[CH:3]=1.Cl.I([O-])(=O)(=O)=[O:26].[Na+].[OH-].[Na+]>O.C(Cl)Cl>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][CH2:21][S:22]([CH3:23])=[O:26])[CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 124098Metoclopramide sulfideHCID 23667635Sodium periodate

生成物 1

HCID 98229474-Amino-5-chloro-N-(2-(diethylamino)ethyl)-2-(2-(methylsulfinyl)ethoxy)benzamide収率 93.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-[2-(methylthio)ethoxy]benzamide (1.0 g, 2.28 mmoles) (prepared in Example 20) and 1.4N HCl solution (3.97 ml, 5.56 mmoles) in 15 ml of H2O at 0°-5°, was added sodium metaperiodate (0.625 g, 2.92 mmoles). The mixture, which soon began to darken, was stirred at 0°-5° to 2 hours. The mixture was then diluted to 50 ml and made alkaline (pH=12) with NaOH solution. Methylene chloride (50 ml) was added, the mixture was shaken well, and the layers were separated. The aqueous layer was extracted with 3 portions of methylene chloride and the combined organic solutions were dried (anhydrous MgSO4) and evaporated. A dark oil (0.96 g) which solidified upon standing was obtained. The crude product was flash chromatographed on silica, eluting with CH2Cl2 :CH3OH:NH4OH, 80:20:0.5. Appropriate fractions were combined and evaporated to give 0.80 g (77%) of the title compound as a yellow resin which crystallized upon standing, mp. 110°-114°.

後処理

  1. additionThe mixture was then diluted to 50 ml
  2. stirringthe mixture was shaken well
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with 3 portions of methylene chloride
  5. dry with materialthe combined organic solutions were dried (anhydrous MgSO4)
  6. customevaporated
  7. customupon standing was obtained
  8. customchromatographed on silica
  9. washeluting with CH2Cl2
  10. customevaporated

出典と根拠

ORDレコード
ord-fffe0988110646bba3dba7abb164c8f1
出典データセット
uspto-grants-1989_04
特許番号
US04820715

関連ノート

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