Methyl iodide → HCID 14801186, compound

HRID 1709329Notes

Reaction equation

HRID 1709329 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:5]([CH3:14])=[C:6]([CH:8]=[CH:9][C:10]=1[S:11][C:12]#N)[NH2:7].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].CI>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[C:5]([CH3:14])=[C:6]([CH:8]=[CH:9][C:10]=1[S:11][CH3:12])[NH2:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 73972Sodium sulfide nonahydrateHCID 14801185HCID 14801185, compound

Product 1

HCID 14801186HCID 14801186, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

29.1 g (0.14 mol) of 3-methoxymethyl-2-methyl-4-thiocyanoaniline was dissolved in 200 ml of ethanol and mixed with 100 ml of an aqueous solution containing 33.6 g of sodium sulfide nonahydrate at room temperature. Then, 21.9 g of methyl iodide was dropwise added thereto, and the mixture was reacted at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and water and chloroform were added to the residue. Then, the organic layer was separated and washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 25.6 g of the desired product as an oily substance.

Workup

  1. customthe mixture was reacted at room temperature for 3 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off under reduced pressure, and water and chloroform
  4. additionwere added to the residue
  5. customThen, the organic layer was separated
  6. washwashed sequentially with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-646aa69b50204a2c8d7e833a670f0795
Source dataset
uspto-grants-1990_08
Patent number
US04948887

Reaction notes

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