Glycine → N-[(Methylthio)thioxomethyl]glycine

HRID 895052Notes

Reaction equation

HRID 895052 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[K+].[C:8](=[S:10])=[S:9].[CH3:11]I>C(O)C.O>[C:3]([CH2:2][NH:1][C:8](=[S:10])[S:9][CH3:11])([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 750GlycineHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide

Product 1

HCID 3960879N-[(Methylthio)thioxomethyl]glycine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Glycine (60 g., 0.8 mol.) was added to a cooled (5°-10°) solution of 89.6 g. (1.6 mol.) of potassium hydroxide in 200 ml. of water. After complete dissolution 60.8 g. (0.8 mol.) of carbon disulfide was added and the reaction mixture was stirred at 25° for three hours. A solution of 113.6 g. (0.8 mol.) of methyl iodide in 200 ml. of ethanol was added while maintaining the temperature at 25°-30°. The reaction mixture was stirred for two hours at 25°, then concentrated in vacuo and the remaining aqueous phase was basicified to pH 8.0 with aqueous sodium carbonate and extracted with ether. The aqueous phase was acidified to pH 2.5 with dilute hydrochloric acid and extracted with ethyl acetate. The extract was concentrated in vacuo and the residue recrystallized from toluene to give methyl carboxymethyldithiocarbamate.

Workup

  1. temperaturea cooled (5°-10°) solution of 89.6 g
  2. dissolutionAfter complete dissolution 60.8 g
  3. temperaturewhile maintaining the temperature at 25°-30°
  4. stirringThe reaction mixture was stirred for two hours at 25°
  5. concentrationconcentrated in vacuo
  6. extractionextracted with ether
  7. extractionextracted with ethyl acetate
  8. concentrationThe extract was concentrated in vacuo
  9. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-ac84f552a2674643b440ac38e2550d19
Source dataset
uspto-grants-1981_08
Patent number
US04286089

Reaction notes

Loading…