Oxalic Acid → (3-Benzenesulfonyl-propyl)-[2-(2-ethoxy-phenoxy)-ethyl]-amine oxalate

HRID 1004663Notes

Reaction equation

HRID 1004663 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[CH2:14]([O:16][C:17]1[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=1[O:19][CH2:20][CH2:21][NH2:22])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35]>C(C(C)=O)C>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[C:8]1([S:5]([CH2:4][CH2:3][CH2:2][NH:22][CH2:21][CH2:20][O:19][C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[O:16][CH2:14][CH3:15])(=[O:7])=[O:6])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 11430Potassium CarbonateHCID 53030422-(2-Ethoxyphenoxy)ethylamineHCID 12518323(3-Bromopropanesulfonyl)benzene

Product 1

HCID 9890134(3-Benzenesulfonyl-propyl)-[2-(2-ethoxy-phenoxy)-ethyl]-amine oxalateYield 7.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of [(3-bromopropyl)sulfonyl]benzene (26.3 g, 100 mmol), 2-(2-ethoxyphenoxy)ethanamine (18.1 g, 100 mmol), and potassium carbonate (55.3 g, 400 mmol) in 200 mL of methyl ethyl ketone is heated at reflux for 18 hours. The reaction mixture is cooled, filtered, and the filtrate is evaporated. The residue is dissolved in warm 2-propanol and treated with oxalic acid (9.3 g, 101 mmol). The precipitated salt is filtered and recrystallized from 2-propanol to yield 3.2 g (7%) of product, mp 184-188° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customthe filtrate is evaporated
  6. dissolutionThe residue is dissolved in warm 2-propanol
  7. filtrationThe precipitated salt is filtered
  8. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-58b84fcc4561460eb8f276b11a8009ec
Source dataset
uspto-grants-2000_04
Patent number
US06051605

Reaction notes

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