Sodium Hydroxide → 2-({[3-(Trifluoromethyl)phenyl]sulfanyl}methyl)pyridine--hydrogen chloride (1/1)

HRID 1649133Notes

Reaction equation

HRID 1649133 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([SH:9])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].Cl.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][Cl:22]>C(O)C>[ClH:22].[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[C:5]([S:9][CH2:21][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 1367513-(Trifluoromethyl)benzenethiol

Product 1

HCID 129532902-({[3-(Trifluoromethyl)phenyl]sulfanyl}methyl)pyridine--hydrogen chloride (1/1)Yield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

m-Trifluoromethylbenzenethiol (5 g) was added to a solution of NaOH (2.25 g) in ethanol (50 ml) and the resulting solution was treated with a solution of 2-picolyl chloride, hydrochloride (4.6 g) in ethanol (25 ml) and the mixture was stirred for 5 hours. The resulting suspension was filtered through kieselghur and the solvent was removed by evaporation. The residue was converted into the hydrochloride in ether with ethereal HCl and recrystallised from acetoneether to give 2-(((3-trifluoromethylphenyl)thio)methyl)pyridine hydrochloride (4.8 g) mp 145°-6° C. Found: C,51.1; H,4.0; N,4.7. C13H10F3NS.HCl requires C,51.0; H,3.6; N,4.6%).

Workup

  1. filtrationThe resulting suspension was filtered through kieselghur
  2. customthe solvent was removed by evaporation
  3. customrecrystallised from acetoneether

Sources & evidence

ORD record
ord-533ef9704e9945e4adf1ebe5cd346388
Source dataset
uspto-grants-1983_11
Patent number
US04415579

Reaction notes

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