Methyl iodide → HCID 1704438, compound

HRID 2202630Notes

Reaction equation

HRID 2202630 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](N(CC)CC)C.[CH:13]1([N:19]=[C:20]=[S:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CI>CN(C=O)C>[CH:13]1([NH:19][C:20](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[S:21][CH3:6])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 8471TriethylamineHCID 14289Cyclohexyl isothiocyanate2×

Product 1

HCID 1704438HCID 1704438, 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 Cyclohexyl isothiocyanate (1 eq) dropwise, then stirred until complete by TLC (absence of Cyclohexyl isothiocyanate, 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-((cyclohexylamino)(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-7807db1c4dd94afc803306018ca93af0
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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