Oxalic Acid → N,N-Diethyl-N'-[2-(phenylsulfonyl)ethyl]-1,4-butanediamine oxalate hydrate

HRID 330398

Reaction equation

HRID 330398 reaction equation
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[CH2:13]([N:15]([CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])[CH2:16][CH3:17])[CH3:14].[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>C(#N)C>[OH2:5].[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH2:13]([N:15]([CH2:16][CH3:17])[CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5])[CH3:14]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 117976N,N-Diethyl-1,4-butanediamine

Product 1

HCID 19869533N,N-Diethyl-N'-[2-(phenylsulfonyl)ethyl]-1,4-butanediamine oxalate hydrateYield 164.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 28.2 g (0.138 mole) of [(2-chloroethyl)sulfonyl]benzene and 20.0 g (0.139 mole) of 4-(N,N-diethylamino)-1-butanamine in 700 ml of acetonitrile was stirred at room temperature 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 magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in methanol, a solution of 25.0 g (0.278 mole) of oxalic acid was added and a precipitate was collected to give 47.69 g (68.9%) of title compound, a white crystalline solid, mp 158°-165° C. with decomposition.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methanol
  6. customa precipitate was collected

Sources & evidence

ORD record
ord-c6dccbefbc6a4abbadf02e99b7bdf981
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Linked notes

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