Sodium Hydroxide → 1-Methyl-N-[2-(1-naphthalenesulfinyl)ethyl]ethanamine, hydrochloride

HRID 745157ノート

反応式

HRID 745157 の反応式
[ClH:1].[CH3:2][CH:3]([NH:5][CH2:6][CH2:7][S:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:4].B1([O-])O[O:20]1.O.O.O.O.[Na+].[OH-].[Na+]>S(=O)(=O)(O)O>[ClH:1].[CH3:4][CH:3]([NH:5][CH2:6][CH2:7][S:8]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:20])[CH3:2]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 136550411-methyl-N-[2-(1-naphthalenylthio)ethyl]ethanamine hydrochlorideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

生成物 1

HCID 136550491-Methyl-N-[2-(1-naphthalenesulfinyl)ethyl]ethanamine, hydrochloride収率 9.1%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

A solution of 12.0 g (0.043 mole) of 1-methyl-N-[2-(1-naphthalenylthio)ethyl]ethanamine hydrochloride and 19.7 g (0.028 mole) of sodium perborate tetrahydrate in 500 ml of 2N sulfuric acid was stirred overnight at room temperature. The solution was poured over ice and the mixture was made alkaline with 50% sodium hydroxide and then extracted with chloroform. The chloroform layer was evaporated to give a dark-brown oil, the free base of the title compound, which crystallized at room temperature. A one gram sample was reacted with ethereal hydrogen chloride and recrystallized from methanol-diethyl ether to give 0.72 g (9.1%) of white solid, m.p. 153°-155° C.

後処理

  1. additionThe solution was poured over ice
  2. extractionextracted with chloroform
  3. customThe chloroform layer was evaporated
  4. customto give a dark-brown oil
  5. customthe free base of the title compound, which crystallized at room temperature
  6. customA one gram sample was reacted with ethereal hydrogen chloride
  7. customrecrystallized from methanol-diethyl ether

出典と根拠

ORDレコード
ord-8beacc982f0849418b89314cf2440ef1
出典データセット
uspto-grants-1986_07
特許番号
US04597902

反応ノート

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