Sodium Hydroxide → 2-{[(3,4-Dichlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

HRID 2286221Notes

Reaction equation

HRID 2286221 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19]Cl>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23392Picolyl chloride hydrochlorideHCID 799643,4-Dichlorobenzenethiol

Product 1

HCID 127602202-{[(3,4-Dichlorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)Yield 128.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3,4-Dichlorobenzenethiol (5 g) was added to a solution of sodium hydroxide (2.25 g) in ethanol (50 ml) and the resulting solution was treated with 2-picolyl chloride, hydrochloride (4.6 g) in ethanol (25 ml). After stirring for 4 hours at ambient temperature the mixture was filtered and the solvent removed by evaporation. The residue was converted into the hydrochloride with ethereal HCl and this was recrystallised from ethanol/ether to give 2-(((3,4-dichlorophenyl)thio)methyl)pyridine, hydrochloride (5.5 g) mp 213°-4° C. (Found: C,46.7; H,3.3; N,4.4 C12H9Cl2NS.HCl requires C,47.0; H,3.3; N,4.6%).

Workup

  1. filtrationwas filtered
  2. customthe solvent removed by evaporation
  3. customthis was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-52e8eb23264d44f58b199ad9362b884d
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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