4-Fluoroaniline → Methyl 2-cyano-3-[(4-fluorophenyl)amino]-3-(methylsulfanyl)-2-propenoate

HRID 1724643Notes

Reaction equation

HRID 1724643 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][S:10][C:11](SC)=[C:12]([C:17]#[N:18])[C:13]([O:15][CH3:16])=[O:14]>>[C:17]([C:12](=[C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[S:10][CH3:9])[C:13]([O:15][CH3:16])=[O:14])#[N:18]

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 319957Methyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate

Product 1

HCID 68934483Methyl 2-cyano-3-[(4-fluorophenyl)amino]-3-(methylsulfanyl)-2-propenoate

Conditions

Temperature
150 °C

Procedure

0.5 g (4.5 mmol) of 4-fluoroaniline is thoroughly mixed with 0.91 g (4.5 mmol) of methyl 3,3-bis(methylthio)-2-cyanoacrylate (R. Gompper, W. Toepfl, Chem. Ber. 1962, 95, 2861-2870). The reaction mixture is heated at 150° C. for 2 h, resulting in a melt. After cooling, a pale solid is obtained and is washed several times with methanol. 0.68 g (55.7% of theory) of the desired product is obtained.

Workup

  1. customresulting in a melt
  2. temperatureAfter cooling
  3. customa pale solid is obtained
  4. washis washed several times with methanol

Sources & evidence

ORD record
ord-4c076426cc3d473ca45653a612f13bec
Source dataset
uspto-grants-2009_02
Patent number
US07488733B2

Reaction notes

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