Methyl isothiocyanate → HCID 13208309, compound

HRID 262563Notes

Reaction equation

HRID 262563 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[SH:5][CH2:6][CH2:7][C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9]>N1C=CC=CC=1.[OH-].[Na+]>[CH3:1][NH:2][C:3]([S:5][CH2:6][CH2:7][C:8]([N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=[O:13])=[O:9])=[S:4]

Participants

5

Reactant 2

HCID 11167Methyl isothiocyanateHCID 999781-(3-Mercapto-1-oxopropyl)-L-proline

Product 1

HCID 13208309HCID 13208309, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methylisothiocyanate (4 g) is added to a solution of 3-mercaptopropanoyl-L-proline (10.1 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 ethyl acetate. The organic phase is concentrated to dryness to yield 1-[3-[[(methylamino)thiocarbonyl]thio]propanoyl]-L-proline.

Workup

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

Sources & evidence

ORD record
ord-f03a86a929f74bb5aa135211f05f2596
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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