Methyl iodide → HCID 1704453, compound

HRID 527252Notes

Reaction equation

HRID 527252 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[C:6]1([N:12]=[C:13]=[S:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:15]I>CN(C=O)C>[CH3:15][S:14][C:13]([NH:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[C:2]([C:1]#[N:5])[C:3]#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 7673Phenyl IsothiocyanateHCID 8010Malononitrile

Product 1

HCID 1704453HCID 1704453, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of malononitrile (1.0 g, 15.14 mmol) in DMF 20 mL was added TEA (2.099 mL, 15.14 mmol). After the mixture was stirred at room temperature for 5 min, phenylisothiocynate (2.047 g, 15.14 mmol) was added dropwise to the mixture. The reaction mixture was stirred at room temperature for 30 min. After the reaction was complete as determined by TLC, methyl iodide (2.149 g, 15.14 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr, at which time the reaction was complete as determined by TLC. The reaction mixture was poured into 100 mL ice water. The resulting precipitate was filtered and dried in an oven overnight to give compound 6 (3.226 g, 98.2% yield, 97.4% purity) as a light yellow solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 min
  2. additionwas added
  3. stirringthe reaction mixture was stirred at room temperature for 1 hr, at which time the reaction
  4. filtrationThe resulting precipitate was filtered
  5. customdried in an oven overnight

Sources & evidence

ORD record
ord-fcdb4ff728074f9f8c25e260312e43c8
Source dataset
uspto-grants-2016_05
Patent number
US09346792B2

Reaction notes

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