Hydrochloric Acid → HCID 20148341, compound

HRID 2290958Notes

Reaction equation

HRID 2290958 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>[Cl-: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 20148341HCID 20148341, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

Chlorine (76.0 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. 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 to precipitate the anilinium chloride salt. 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-(trifluoromethyl) anilinium chloride.

Workup

  1. temperaturewhile maintaining the reaction temperature below 20° C
  2. customwas obtained
  3. customExcess water was removed by azeotropic distillation (780 ml of solvent were removed)
  4. temperaturethe resulting solution was cooled to 0° C. with a steady stream of HCl bubbling through
  5. customto precipitate the anilinium chloride salt
  6. filtrationFiltration
  7. washwashing of the solids with 150 ml
  8. dry with materialof cold ethylene dichloride and air-drying

Sources & evidence

ORD record
ord-c22510bb8f7c4066933c6a0b6c2bdd7e
Source dataset
uspto-grants-1986_10
Patent number
US04618713

Reaction notes

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