Methyl iodide → HCID 1704453, compound

HRID 2202618Notes

Reaction equation

HRID 2202618 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](N(CC)CC)C.[C:13]1([N:19]=[C:20]=[S:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CI>CN(C=O)C>[CH3:6][S:21][C:20]([NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7673Phenyl Isothiocyanate2×HCID 8010MalononitrileHCID 8471Triethylamine

Product 1

HCID 1704453HCID 1704453, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved malononitrile (5.0 g) in DMF (50 mL), added triethylamine (1 eq., 10.49 mL), and stirred for 5 minutes before adding phenylisothiocyanate (1 eq) dropwise, then stirred until complete by TLC (absence of phenylisothiocyanate, 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-((methylthio)(phenylamino)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-365a9e696cf641e586d8b5ff61b6cb53
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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