Methanol → Ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate

HRID 2401966Notes

Reaction equation

HRID 2401966 reaction equation
[CH3:1][S:2][C:3](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[S:4][CH3:5].C([CH:13](S)[C:14]([O-])=[O:15])C.[CH3:18][OH:19]>>[NH2:8][C:7]1[C:6]([C:9]#[N:10])=[C:3]([S:4][CH3:5])[S:2][C:1]=1[C:18]([O:15][CH2:14][CH3:13])=[O:19]

Participants

4

Reactant 3

HCID 887MethanolHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 22075691HCID 22075691, compound

Product 1

HCID 474798Ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylateYield 99%

Procedure

A mixture of [bis(methylsulfanyl)methylene]malononitrile (40 g, 230 mmol), ethylthioglycolate (29 g, 230 mmol) and TEA (24 mL, 173 mmol) in MeOH (600 mL) was allowed to stir at reflux for 2 h. The reaction mixture was allowed to cool overnight and the precipitate was filtered off then washed with cold MeOH (3×50 mL) to give ethyl 3-amino-4-cyano-5-(methylsulfanyl)thiophene-2-carboxylate (52.4 g, 99%). LCMS: (FA) ES+ 275.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureto cool overnight
  3. filtrationthe precipitate was filtered off
  4. washthen washed with cold MeOH (3×50 mL)

Sources & evidence

ORD record
ord-fbaa99f957734b3f8d45cca61eb312f7
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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