Methyl iodide → HCID 21183157, compound

HRID 848988Notes

Reaction equation

HRID 848988 reaction equation
[CH3:1][C:2]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:7]([S:16][C:17]#N)[CH:6]=[CH:5][C:3]=1[NH2:4].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].CI>C(O)C.O>[CH3:1][C:2]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:7]([S:16][CH3:17])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 73972Sodium sulfide nonahydrateHCID 21183182HCID 21183182, compound

Product 1

HCID 21183157HCID 21183157, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 2.0 g (7.9 mmol) of 2-methyl-3-(2-methylphenyl)-4-thiocyanoaniline in 15 mL of ethanol was added dropwise over a 20-min period with stirring to a solution of 2.2 g of sodium sulfide nonahydrate (9.1 mmol) in 5 mL of water. The mixture was stirred at ambient temperature for 2 hours and was then cooled with an ice/salt bath. A solution of 1.5 g (11 mmol) of methyl iodide in 5 mL of ethanol was added with stirring over a 10-min period. The mixture was diluted with water and the resulting mixture was extracted with ether. The ethereal extract was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The 2.0 g of residue was the title compound of about 80 percent purity.

Workup

  1. temperaturewas then cooled with an ice/salt bath
  2. stirringwith stirring over a 10-min period
  3. extractionthe resulting mixture was extracted with ether
  4. extractionThe ethereal extract
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3941d052b4a54f21812b08786bcba260
Source dataset
uspto-grants-2000_01
Patent number
US06010981

Reaction notes

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