Methyl iodide → HCID 7718564, compound

HRID 2202627Notes

Reaction equation

HRID 2202627 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6](N(CC)CC)C.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[S:24])=[CH:18][CH:17]=1)([O-:15])=[O:14].CI>CN(C=O)C>[CH3:6][S:24][C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=1)=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8010MalononitrileHCID 8471TriethylamineHCID 75044Benzene, 1-isothiocyanato-4-nitro-2×

Product 1

HCID 7718564HCID 7718564, 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-nitrophenyl isothiocyanate (1 eq) dropwise, then stirred until complete by TLC (absence of 4-Nitrophenyl isothiocyanate, 3 hrs). Added methyl iodide (1 eq) dropwise, then stirred until intermediate was fully consumed (absent on TLC, 18 hrs); poured into 500 mL ice water, then filtered resulting solution to obtain 2-((methylthio)((4-nitrophenyl)amino)methylene)malononitrile as a white powder.

Workup

  1. customwas fully consumed (absent on TLC, 18 hrs)
  2. additionpoured into 500 mL ice water
  3. filtrationfiltered
  4. customresulting solution

Sources & evidence

ORD record
ord-ee7a5c069d9b4170a37508e784f64689
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

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