Methyl iodide → 2-Methylthio-3,5-dicyano-4-methoxythiophene

HRID 982015Notes

Reaction equation

HRID 982015 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]([C:11]#[N:12])=[C:6]([OH:10])[C:7]=1[C:8]#[N:9].CI.[C:15](=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>C(#N)C>[CH3:1][S:2][C:3]1[S:4][C:5]([C:11]#[N:12])=[C:6]([O:10][CH3:15])[C:7]=1[C:8]#[N:9]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 141197702-Methylthio-3,5-dicyano-4-hydroxythiophene

Product 1

HCID 141197712-Methylthio-3,5-dicyano-4-methoxythiophene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6 g of 2-methylthio-3,5-dicyano-4-hydroxythiophene 10 ml of methyl iodide, 10 g of potassium carbonate, and 3 ml of triethylamine are refluxed in 300 ml of acetonitrile while stirring. After 2 hours the reaction mixture is filtered warm and evaporated to dryness. The residue is taken up in 200 ml of methylene chloride and washed successively with a solution of potassium carbonate in water and with water. The methylene chloride solution is then dried and evaporated to dryness. After recrystallisation of the residue from isopropanol, the desired product is obtained in a yield of 4.0 g; melting-point 132° C.

Workup

  1. filtrationAfter 2 hours the reaction mixture is filtered
  2. temperaturewarm
  3. customevaporated to dryness
  4. washwashed successively with a solution of potassium carbonate in water and with water
  5. dry with materialThe methylene chloride solution is then dried
  6. customevaporated to dryness
  7. customAfter recrystallisation of the residue from isopropanol

Sources & evidence

ORD record
ord-0887362eb0574398a66fd717bf5a366f
Source dataset
uspto-grants-1991_02
Patent number
US04994485

Reaction notes

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