Methyl iodide → HCID 13573165, compound

HRID 2202623Notes

Reaction equation

HRID 2202623 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[S:22])=[CH:16][CH:15]=1.CI>CN(C=O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[S:22][CH3:6])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 8471TriethylamineHCID 164804-Chlorophenyl isothiocyanate2×

Product 1

HCID 13573165HCID 13573165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved malononitrile (5.0 g) in DMF (50 mL), added triethylamine (1 eq), and stirred for 5 minutes before adding 4-chlorophenylisothiocyanate (1 eq) dropwise, then stirred until complete by TLC (absence of 4-chlorophenylisothiocyanate, 3 hrs). Added methyl iodide (1 eq) dropwise, then stirred until intermediate was fully consumed (absent on TLC, 18 hrs); poured into 100 mL ice water, then filtered resulting solution to obtain 2-(((4-chlorophenyl)amino)(methylthio)methylene)malononitrile as a white powder.

Workup

  1. customwas fully consumed (absent on TLC, 18 hrs)
  2. additionpoured into 100 mL ice water
  3. filtrationfiltered
  4. customresulting solution

Sources & evidence

ORD record
ord-a0b4e26546fc43cb92a59d563e1e9975
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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