Glycine → HCID 178505159, compound

HRID 1649866Notes

Reaction equation

HRID 1649866 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[N:20][S:21]([CH3:24])(=[O:23])=[O:22])SC)=[CH:12][CH:11]=1)#[N:9]>O.C(O)C>[CH3:24][S:21]([N:20]=[C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]#[N:9])=[CH:11][CH:12]=1)[NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[O:23])=[O:22]

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 56613771HCID 56613771, compound

Product 1

HCID 178505159HCID 178505159, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.57 g (7.6 mol) of glycine, of 0.3 g (7.6 mmol) of sodium hydroxide in 3 cm3 of water and of 2.0 g (7.6 mmol) of N-(4-cyanophenyl)-N'-methylsulfonyl-S-methylisothiourea in 30 cm3 of 95% ethanol is heated at boiling point for 7 hours. After cooling, the precipitate obtained is filtered and dissolved in 20 cm3 of a 1N sodium hydroxide solution. The solution obtained is washed with dichloromethane (3×10 cm3) and ethyl acetate (2×10 cm3) then acidified to a pH close to 3 with a 6N HCl solution. After cooling, the precipitate obtained is filtered, washed with water (2×5 cm3) and dried in vacuo to give N-[methylsulfonylimino(4-cyanophenylamino)methyl]-2-aminoethanoic acid (yield 55%) having a melting point of 170° C.

Workup

  1. customfor 7 hours
  2. temperatureAfter cooling
  3. customthe precipitate obtained
  4. filtrationis filtered
  5. dissolutiondissolved in 20 cm3 of a 1N sodium hydroxide solution
  6. customThe solution obtained
  7. washis washed with dichloromethane (3×10 cm3) and ethyl acetate (2×10 cm3)
  8. customclose to 3 with a 6N HCl solution
  9. temperatureAfter cooling
  10. customthe precipitate obtained
  11. filtrationis filtered
  12. washwashed with water (2×5 cm3)
  13. customdried in vacuo

Sources & evidence

ORD record
ord-9f28cf1469da400794938187462bac62
Source dataset
uspto-grants-1990_05
Patent number
US04921939

Reaction notes

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