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

HRID 262562Notes

Reaction equation

HRID 262562 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-ec207723872543b8966f7a84531bea44
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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