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

HRID 745157

반응식

HRID 745157 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8beacc982f0849418b89314cf2440ef1
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04597902

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