Beta-Alanine → N-[4-cyanophenylamino(imino)methyl]-3-aminopropanoic acid

HRID 2352651Notes

Reaction equation

HRID 2352651 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].I.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[NH:22])SC)=[CH:14][CH:13]=1)#[N:11]>O.C(O)C>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[NH:22])[NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[CH:16][CH:17]=1)#[N:11]

Participants

6

Reactant 3

HCID 239Beta-AlanineHCID 14798Sodium HydroxideHCID 178504005N-(4-cyanophenyl)-S-methylisothiourea hydroiodide

Product 1

HCID 178510066N-[4-cyanophenylamino(imino)methyl]-3-aminopropanoic acidYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4.18 g (47 mmol) of β-alanine, of 1,88 g (47 mmol) of sodium hydroxide in 20 cm3 of water and of 15 g (47 mmol) of N-(4-cyanophenyl)-S-methylisothiourea hydroiodide in 100 cm3 of 95% ethanol is heated to reflux for 5 hours. The precipitate formed is filtered, then dissolved in 150 cm3 of 1N aqueous sodium hydroxide solution. The solution obtained is washed with ethyl acetate (3×50 cm3), then neutralized to pH 7 by a concentrated HCl solution. The precipitate obtained is filtered, washed with hot absolute ethanol, then recrystallized in water. 7 g (yield 65%) of N-[4-cyanophenylamino(imino)methyl]-3-aminopropanoic acid, having a melting point of 233°-235° C., are obtained.

Workup

  1. temperatureto reflux for 5 hours
  2. customThe precipitate formed
  3. filtrationis filtered
  4. dissolutiondissolved in 150 cm3 of 1N aqueous sodium hydroxide solution
  5. customThe solution obtained
  6. washis washed with ethyl acetate (3×50 cm3)
  7. customThe precipitate obtained
  8. filtrationis filtered
  9. washwashed with hot absolute ethanol
  10. customrecrystallized in water

Sources & evidence

ORD record
ord-9bcbb530424a450caab8698323bd9d2d
Source dataset
uspto-grants-1989_10
Patent number
US04877895

Reaction notes

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