Methyl iodide → 2-(((3-Chlorophenyl)amino)(methylthio)methylene)malononitrile

HRID 1049172Notes

Reaction equation

HRID 1049172 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[Cl:6][C:7]1[CH:8]=[C:9]([N:13]=[C:14]=[S:15])[CH:10]=[CH:11][CH:12]=1.[CH3:16]I>CN(C=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[S:15][CH3:16])[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 754493-Chlorophenyl isothiocyanate

Product 1

HCID 149501572-(((3-Chlorophenyl)amino)(methylthio)methylene)malononitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved malononitrile (3.328 g) in DMF (35 mL), added TEA (1 eq., 6.983 mL), and stirred for 5 minutes before adding 3-chlorophenylisothiocyante (1 eq., 8.54 mL) dropwise, then stirred until complete by TLC (absence of 3-chlorophenylisothiocyanate, 3 hrs). Added methyl iodide (1 eq., 3.136 mL) dropwise, then stirred until intermediate was fully consumed (absent on TLC, 18 hrs); poured into 500 mL ice water, then filtered resulting solution to 2-(((3-chlorophenyl)amino)(methylthio)methylene)malononitrile as a white powder.

Workup

  1. additionbefore adding 3-chlorophenylisothiocyante (1 eq., 8.54 mL) dropwise
  2. customwas fully consumed (absent on TLC, 18 hrs)
  3. additionpoured into 500 mL ice water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0f2a8aeac40845d6850561020d95c149
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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