Glycine → HCID 178510067, compound

HRID 1649863Notes

Reaction equation

HRID 1649863 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]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])SC)=[CH:12][CH:11]=1)#[N:9]>O.C(O)C>[C:24]1([S:21]([N:20]=[C:17]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([C:8]#[N:9])=[CH:15][CH:14]=2)[NH:1][CH2:2][C:3]([OH:5])=[O:4])(=[O:23])=[O:22])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 56637441HCID 56637441, compound

Product 1

HCID 178510067HCID 178510067, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.57 g (7.6 mmoles) of glycine and 0.3 g (7.6 mmoles) of sodium hydroxide in 3 cm3 of water and 2.5 (7.6 mmoles) of N-(4-cyanophenyl)-N'-phenylsulfonyl-S-methylisothiourea in 30 cm3 of 95% ethanol is heated to boiling for 7 hours. After cooling, the precipitate obtained is filtered and dissolved in 20 cm3 of 1N sodium hydroxide solution. The solution obtained is washed with dichloromethane (3×10 cm3) and ethyl acetate (2×10 cm3) and is then acidified to pH 3 with a 6N HCl solution. After cooling, precipitate forms and is filtered, washed with water (2×5 cm3) and dried in vacuo to give 1.4 g (yield 52%) of N-[phenylsulfonylimino(4-cyanophenylamino)methyl]-2-aminoethanoic acid having a melting point of 133° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling
  3. customthe precipitate obtained
  4. filtrationis filtered
  5. dissolutiondissolved in 20 cm3 of 1N sodium hydroxide solution
  6. customThe solution obtained
  7. washis washed with dichloromethane (3×10 cm3) and ethyl acetate (2×10 cm3)
  8. temperatureAfter cooling
  9. filtrationprecipitate forms and is filtered
  10. washwashed with water (2×5 cm3)
  11. customdried in vacuo

Sources & evidence

ORD record
ord-066273b966054201aceef428b8ccfd21
Source dataset
uspto-grants-1990_05
Patent number
US04921939

Reaction notes

Loading…