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

HRID 330395
Notes
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Reaction equation

HRID 330395 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
2×
HCID 3283Diethyl EtherSolvent
HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-bcff8b349aab40b9b5a7f15dcfc6c44d
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04895840

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes