Methanethiol → Propanedinitrile, [(methylthio)[(phenylmethyl)amino]methylene]-

HRID 1602224Notes

Reaction equation

HRID 1602224 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][S:10][C:11](SC)=[C:12]([C:15]#[N:16])[C:13]#[N:14].CS>C(OCC)(=O)C>[CH2:1]([NH:8][C:11]([S:10][CH3:9])=[C:12]([C:15]#[N:16])[C:13]#[N:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 7504BenzylamineHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrile

Product 1

HCID 1704435Propanedinitrile, [(methylthio)[(phenylmethyl)amino]methylene]-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

43.6 ml (400 mmol) of benzylamine are added to a suspension of 68.4 g (400 mmol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile [3,3-bis(methylsulfanyl)-2-cyano-acrylonitrile] (Maybridge) in 400 ml of ethyl acetate. The clear solution is heated slowly to 70° C. (→ evolution of MeSH!), stirred at that temperature for 1.5 hours, cooled to RT and concentrated by evaporation, yielding crystalline 3-benzylamino-3-methylmercapto-2-cyano-acrylonitrile; 1H-NMR: (CD3OD) 7.36 (m, 5H), 4.77 (s, 2H), 2.59 (s, 3H).

Workup

  1. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1a04caa47906408abdf7e2f8bffd6b18
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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