4-Chloro-2-toluidine → HCID 54103172, compound

HRID 266533Notes

Reaction equation

HRID 266533 reaction equation
N(OC(C)(C)C)=O.[Cl:8][C:9]1[CH:15]=[CH:14][C:12](N)=[C:11]([CH3:16])[CH:10]=1.[CH3:17][S:18]SC>C(Cl)(Cl)Cl>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([S:18][CH3:17])=[C:11]([CH3:16])[CH:10]=1

Participants

5

Reactant 3

HCID 72514-Chloro-2-toluidine3×HCID 10906Tert-Butyl nitrite3×HCID 12232Dimethyl Disulfide2×

Product 1

HCID 54103172HCID 54103172, compoundYield 908.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Conditions

Temperature
70 °C

Procedure

t-Butyl nitrite (1.52 g) was added to a mixture of 4-chloro-2-methylaniline (2.0 g) and dimethyl disulphide (14.49 g) in chloroform. The mixture was heated to 70° C. to initiate the reaction. A solution of 4-chloro-2-methylaniline (9.0 g) in chloroform and t-butyl nitrite (7.25 g) were added simultaneously while maintaining the temperature in the range 60°-70° C. Further dimethyl disulphide (11.83 g) was added followed by the simultaneous addition of a solution of 4-chloro-2-methylaniline (9.0 g) in chloroform and t-butyl nitrite (7.25 g) while maintaining the temperature in the range 50°-55° C. The mixture was stirred at room temperature for 2 hours. It was washed thoroughly with water, 2M hydrochloric acid, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 5-chloro-2-(methylsulphenyl)toluene (22.15 g) as a red oil which was not further characterized.

Workup

  1. customthe reaction
  2. temperaturewhile maintaining the temperature in the range 60°-70° C
  3. temperaturewhile maintaining the temperature in the range 50°-55° C
  4. washIt was washed thoroughly with water, 2M hydrochloric acid, water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-80af69d270c54662a39ca96a80688b1b
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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