Beta-Alanine → HCID 178512322, compound

HRID 2352649Notes

Reaction equation

HRID 2352649 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[C:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[N:21][C:22]#[N:23])SC)=[CH:13][CH:12]=1)#[N:10]>O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:22]([N:21]=[C:18]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]#[N:10])=[CH:12][CH:13]=1)[NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])#[N:23]

Participants

7

Reactant 3

HCID 239Beta-AlanineHCID 14798Sodium HydroxideHCID 178503891HCID 178503891, compound

Product 1

HCID 178512322HCID 178512322, compoundYield 63.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 12.3 g (0.138 mol) of β-alanine and of 5.52 g (0.138 mol) of sodium hydroxide in 100 cm3 of water is added to a solution of 20 g (0.092 mol) of N-(4-cyanophenyl)-N'-cyano-S-methylisothiourea in 300 cm3 of 95% ethanol. The mixture is heated to reflux for 4 hours. After cooling, the solution is filtered then concentrated to dryness in vacuo. The residue obtained is dissolved in 200 cm3 of a 2% sodium carbonate solution. The resulting solution is washed by dichloromethane (3×50 cm3) then acidified by a 3N HCl solution until a pH close to 2 is obtained. The white solid formed is filtered, then washed with water (2×10 cm3) and dried in vacuo. After recrystallization in water, 15 g (yield 63%) of N-[cyanoimino(4-cyanophenylamino)methyl]-3-aminopropanoic acid, which is a solid having a melting point of 158°-162° C., are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. filtrationthe solution is filtered
  5. concentrationthen concentrated to dryness in vacuo
  6. customThe residue obtained
  7. washThe resulting solution is washed by dichloromethane (3×50 cm3)
  8. customa pH close to 2
  9. customis obtained
  10. customThe white solid formed
  11. filtrationis filtered
  12. washwashed with water (2×10 cm3)
  13. customdried in vacuo
  14. customAfter recrystallization in water

Sources & evidence

ORD record
ord-a0325f6fe8f644f1bb5b2049679aa8ac
Source dataset
uspto-grants-1989_10
Patent number
US04877895

Reaction notes

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