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

HRID 1156765Notes

Reaction equation

HRID 1156765 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 acetone-ether 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 acetone-ether

Sources & evidence

ORD record
ord-ac4c487e66554138bec36ad60c3991e1
Source dataset
uspto-grants-1982_06
Patent number
US04337259

Reaction notes

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