Hydrochloric Acid → 2-Chloromethyl-6-trifluromethyl anilinium hydrochloride

HRID 1719456Notes

Reaction equation

HRID 1719456 reaction equation
[Cl:1]Cl.CS[CH2:5][C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[C:7]=1[NH2:8].[ClH:17].O>C(Cl)CCl>[ClH:1].[Cl:17][CH2:5][C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:15])[F:16])[C:7]=1[NH3+:8]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 24526ChlorineHCID 27359342-Amino-3-(methylthiomethyl)benzotrifluoride

Product 1

HCID 202669222-Chloromethyl-6-trifluromethyl anilinium hydrochlorideYield 92.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

Chlorine (7.60 grams, 1.07 mol) was bubbled into a mechanically stirred solution of 221.0 grams (1.00 mol) of 2-methylthiomethyl-6-trifluoromethyl aniline in 2 liters of ethylene dichloride over 60 minutes while maintaining the reaction temperature below 20° C. A white suspension formed initially, became very thick halfway through the addition, and dissolved to give way to a cloudy solution at the end of the addition. The mixture was then heated to 60° C. while maintaining a steady stream of HCl bubbling through. Water (25 ml, 1.4 mol) was added and the HCl treatment was maintained at 60° C. for 15 minutes at which point a clear solution was obtained. Excess water was removed by azeotropic distillation (780 ml of solvent were removed) and the resulting solution was cooled to 0° C. with a steady stream of HCl bubbling through. Filtration, washing of the solids with 150 ml of cold ethylene dichloride and air-drying gave 228.0 grams (92.7%) of off-white 2-chloromethyl-6-trifluromethyl anilinium hydrochloride. This compound properties and analysis are described above.

Workup

  1. temperaturewhile maintaining the reaction temperature below 20° C
  2. customA white suspension formed initially
  3. additionthrough the addition
  4. dissolutiondissolved
  5. customto give way to a cloudy solution
  6. additionat the end of the addition
  7. customwas obtained
  8. customExcess water was removed by azeotropic distillation (780 ml of solvent were removed)
  9. temperaturethe resulting solution was cooled to 0° C. with a steady stream of HCl bubbling through
  10. filtrationFiltration
  11. washwashing of the solids with 150 ml of cold ethylene dichloride
  12. customair-drying

Sources & evidence

ORD record
ord-b2c3f550049b4b12b9ee337234bc304c
Source dataset
uspto-grants-1985_09
Patent number
US04540522

Reaction notes

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