Glycine → HCID 178512331, compound

HRID 1649862Notes

Reaction equation

HRID 1649862 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[Cl:8][C:9]1[CH:10]=[C:11]([NH:15][C:16](=[N:19][C:20]#[N:21])SC)[CH:12]=[CH:13][CH:14]=1>O.C(O)C>[C:20]([N:19]=[C:16]([NH:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([Cl:8])[CH:10]=1)[NH:1][CH2:2][C:3]([OH:5])=[O:4])#[N:21]

Participants

6

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 178503888HCID 178503888, compound

Product 1

HCID 178512331HCID 178512331, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Three grams (39.9 mmol) of glycine and 1.5 g (37.2 mmol) of sodium hydroxide are mixed in 10 cm3 of water and added to 6 g (26.5 mmol) of N-(3-chlorophenyl)-N'-cyano-S-methylisothiourea in solution in 40 cm3 of 95% ethanol. The mixture is reflux heated for 1 hour. After cooling, the resulting precipitate is filtered and then washed with 2×50 cm3 of ethyl ether. The resulting solid is dissolved in 50 cm3 of 1N sodium hydroxide solution. This solution is washed with 3×10 cm3 of dichloromethane and then acidified with a 3N solution until a pH close to 2 is obtained. The white solid which forms is then filtered and washed in 2×10 cm3 of water, following which it is dried in vacuo. 6 g of N-[cyanoimino(3-clorophenylamino)methyl]-2-aminoethanoic acid (yield 89%) is obtained with a melting point of 109° C.

Workup

  1. temperatureThe mixture is reflux
  2. temperatureheated for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe resulting precipitate is filtered
  5. washwashed with 2×50 cm3 of ethyl ether
  6. dissolutionThe resulting solid is dissolved in 50 cm3 of 1N sodium hydroxide solution
  7. washThis solution is washed with 3×10 cm3 of dichloromethane
  8. customa pH close to 2
  9. customis obtained
  10. filtrationThe white solid which forms is then filtered
  11. washwashed in 2×10 cm3 of water
  12. customis dried in vacuo

Sources & evidence

ORD record
ord-b58491c922484364a053e150ba1009e3
Source dataset
uspto-grants-1990_05
Patent number
US04921939

Reaction notes

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