2-(Bis(methylsulfanyl)methylidene)propanedinitrile → HCID 19610656, compound

HRID 1602286Notes

Reaction equation

HRID 1602286 reaction equation
CS[C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6].[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH2:17])=[CH:14][CH:13]=1>C(O)C>[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:17][C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 4278144-Aminobenzylamine

Product 1

HCID 19610656HCID 19610656, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 17.03 g (0.1 mol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile, 11.34 ml (0.1 mol) of 4-amino-benzylamine (Aldrich) and 60 ml of ethanol is stirred at 50° C. for 2 hours and then concentrated by evaporation in vacuo. Purification of the residue by flash chromatography on silica gel having a particle size of 0.04-0.06 mm using toluene/isopropanol mixtures (49:1, 97:3, 24:1 and 9:1) yields the title compound; m.p. 100-102° C.

Workup

  1. concentrationconcentrated by evaporation in vacuo
  2. customPurification of the residue by flash chromatography on silica gel having a particle size of 0.04-0.06 mm

Sources & evidence

ORD record
ord-d3f6b5c55ef6489cab765c3907dadf96
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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