3-Mercaptopropionic Acid → 3-[(Methylcarbamothioyl)sulfanyl]propanoic acid

HRID 2419430Notes

Reaction equation

HRID 2419430 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[SH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]>N1C=CC=CC=1.[OH-].[Na+]>[CH3:1][NH:2][C:3]([S:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[S:4]

Participants

5

Reactant 2

HCID 65143-Mercaptopropionic AcidHCID 11167Methyl isothiocyanate

Product 1

HCID 35009713-[(Methylcarbamothioyl)sulfanyl]propanoic acid

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methylisothiocyanate (4 g) is added to a solution of 3-mercaptopropanoic acid (5.3 g) in a mixture of pyridine (250 ml) and 0.5 N sodium hydroxide (100 ml). The solution is kept at 40° for two hours and concentrated to dryness in vacuo. The residue is dissolved in water (100 ml.), acidified with concentrated hydrochloric acid and extracted with ether. The organic phase is concentrated to dryness to yield 3-[[(methylamino)thiocarbonyl]thio]propanoic acid, m.p. 86°-87°.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. dissolutionThe residue is dissolved in water (100 ml.)
  3. extractionextracted with ether
  4. concentrationThe organic phase is concentrated to dryness

Sources & evidence

ORD record
ord-56e3ca9edca446d091670f6ab19da817
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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