Hydrochloric Acid → HCID 21183150, compound

HRID 848989Notes

Reaction equation

HRID 848989 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][CH3:17])[CH:6]=[CH:5][C:3]=1N.Cl.N([O-])=O.[Na+].[I-:23].[K+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[I:23][C:3]1[CH:5]=[CH:6][C:7]([S:16][CH3:17])=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:2]=1[CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 24437Sodium SulfiteHCID 21183157HCID 21183157, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21183150HCID 21183150, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of 2.0 g (8.2 mmol) of 85 percent purity 2-methyl-3-(2-methylphenyl)-4-methylthioaniline in 3 mL of dichloromethane was combined with 60 mL of concentrated aqueous hydrochloric acid and the mixture was stirred for 1 hour. It was then cooled to 5° C. A solution of 850 mg (12 mmol) of sodium nitrite in 10 mL of water was added in portions with stirring and cooling. After 45 min, this mixture was poured with stirring into a mixture of a solution of 2.0 g (12 mmol) of potassium iodide in 100 mL of water and 75 mL of dichloromethane and the combination was stirred for 30 min. Five mL of saturated sodium sulfite solution was then added with stirring and after 20 min reaction time, the phases were separated. The organic phase was washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated under reduced pressure. The 2.4 g (83 percent of theory) of oily residue obtained was the title compound in impure form.

Workup

  1. stirringwith stirring
  2. temperaturecooling
  3. waitAfter 45 min
  4. additionthis mixture was poured
  5. stirringthe combination was stirred for 30 min
  6. stirringwith stirring and after 20 min
  7. customreaction time
  8. customthe phases were separated
  9. washThe organic phase was washed with water and with saturated aqueous sodium chloride solution
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe 2.4 g (83 percent of theory) of oily residue obtained

Sources & evidence

ORD record
ord-63aa5a6c1ecb49989f2921f59f8a465e
Source dataset
uspto-grants-2000_01
Patent number
US06010981

Reaction notes

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