2-(Bis(methylsulfanyl)methylidene)propanedinitrile → HCID 21190662, compound

HRID 1068957Notes

Reaction equation

HRID 1068957 reaction equation
CS[C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6].[C:11]([NH:18][CH2:19][CH2:20][NH2:21])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(OCC)(=O)C>[C:11]([NH:18][CH2:19][CH2:20][NH:21][C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

4

Reactant 2

HCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 187201N-BOC-ethylenediamine

Product 1

HCID 21190662HCID 21190662, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 59.8 g (351.2 mmol) of 3,3bis-methylmercapto-2-cyano-acrylonitrile, 56.3 g (351.4 mmol) of N-Boc-ethylenediamine [for preparation see: J. Org. Chem. 60, 4305 (1995)] and 500 ml of ethyl acetate is stirred under reflux for 3 hours and then concentrated in vacuo to approximately half its original volume. The reaction mixture is cooled to 0° C.; 300 ml of diethyl ether are added and the mixture is stirred for a further 0.5 hour and filtered. After washing the filter residue with diethyl ether, 3-[2-(Boc-amino)-ethylamino]-2-cyano-3-methylmercapto-acrylonitrile is obtained; m.p. 123-125° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated in vacuo to approximately half its original volume
  3. addition300 ml of diethyl ether are added
  4. stirringthe mixture is stirred for a further 0.5 hour
  5. filtrationfiltered
  6. washAfter washing the filter residue with diethyl ether

Sources & evidence

ORD record
ord-d03a10f54a8f40eaa02e5079501a864d
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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