Methyl iodide → HCID 86698962, compound

HRID 2202625Notes

Reaction equation

HRID 2202625 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](N(CC)CC)C.[CH:13]1([N:16]=[C:17]=[S:18])[CH2:15][CH2:14]1.ClC1C=CC(N=C=S)=CC=1.CI>CN(C=O)C>[CH:13]1([NH:16][C:17](=[C:2]([C:1]#[N:5])[C:3]#[N:4])[S:18][CH3:6])[CH2:15][CH2:14]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 8471TriethylamineHCID 164804-Chlorophenyl isothiocyanateHCID 92463Cyclopropyl isothiocyanate

Product 1

HCID 86698962HCID 86698962, 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 cyclopropyl isothiocyanate (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-((cyclopropylamino)(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-8be610428cf44fb3a06ec35a3a4db5b1
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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