Methyl isothiocyanate → HCID 13208309, compound

HRID 2419432Notes

Reaction equation

HRID 2419432 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-9623c066c7254c6d89890beb8e4da7db
Source dataset
uspto-grants-1978_08
Patent number
US04105776

Reaction notes

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