Ethanol → 2-[1-(2-Hydroxyethyl)-2-imidazolidinyl-idene]-aminobiphenyl fumarate

HRID 1464036Notes

Reaction equation

HRID 1464036 reaction equation
I.[C:2]1([C:13]2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8]C(=N)SC.[OH:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][NH2:25].[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[CH2:34](O)[CH3:35]>CO>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]/[C:29]([OH:31])=[O:30].[OH:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][NH:25][C:13]1=[C:2]1[CH:3]([NH2:8])[CH:4]=[CH:5][CH:6]=[C:7]1[C:35]1[CH:34]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 444972Fumaric AcidHCID 178503972HCID 178503972, compound

Product 1

HCID 1317183872-[1-(2-Hydroxyethyl)-2-imidazolidinyl-idene]-aminobiphenyl fumarate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(2-biphenylyl)-2-methyl-2-thiopseudourea hydriodide (12 g prepared as described in Example 5) and N-(2-hydroxyethyl)ethylenediamine (10 g) in ethanol (145 ml) was heated under reflux for 165 hours. Removal of the solvent gave an oil which was dissolved in methanol and treated with fumaric acid to give 2-[1-(2-hydroxyethyl)-2-imidazolidinyl-idene]-aminobiphenyl fumarate (m.p. 165°-166° C.) which was recrystallised from a 1:2 mixture of methanol and ether.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 165 hours
  3. customRemoval of the solvent
  4. customgave an oil which

Sources & evidence

ORD record
ord-7676d414f45440c9b06f6714e0dd189a
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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