Sodium Carbonate → N,N-Diethyl-N'-[2-(phenylthio)ethyl]-1,2-ethanediamine maleate

HRID 330395

반응식

HRID 330395 반응식
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29]>C(#N)C.CO.C(OCC)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:12]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 21702((2-Chloroethyl)thio)benzeneHCID 60993N,N-DiethylethylenediamineHCID 444266Maleic Acid

생성물 1

HCID 70360583N,N-Diethyl-N'-[2-(phenylthio)ethyl]-1,2-ethanediamine maleate수율 43.2%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 60.24 g (0.350 mole) of [(2-chloroethyl)thio]benzene, 84 g (0.72 mole) of N,N-diethylethylenediamine, and 80.0 g (0.75 mole) of sodium carbonate in 1.5 liters of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over sodium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in 800 ml of methanol. A solution of approximately 2 equivalents of maleic acid in methanol was added followed by the addition of anhydrous diethyl ether until the solution became slightly cloudy. A white solid precipitated at -5° C. to give 73.15 g (43.2%) of title compound, a white crystalline solid, mp 131°-133° C.

후처리

  1. temperaturewas refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride solution was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customA white solid precipitated at -5° C.

출처 및 근거

ORD 기록
ord-bcff8b349aab40b9b5a7f15dcfc6c44d
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895840

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