m,alpha-Dichlorotoluene → 4-{[(3-Chlorophenyl)methyl]sulfanyl}pyridine

HRID 1758814Notes

Reaction equation

HRID 1758814 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.[SH:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 12103m,alpha-DichlorotolueneHCID 178418431pyridine-4-thiol

Product 1

HCID 134349924-{[(3-Chlorophenyl)methyl]sulfanyl}pyridineYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Chlorobenzyl chloride (1.61 g) and 4-mercaptopyridine (1.11 g) in ethanol (10 ml) were heated at reflux for 4 hours and cooled. Crystals which precipitated were removed by filtration and dried to give the title compound as the hydrochloride (1.3 g) mp 222°-4° C. (Found: C, 52.6; H, 4.3; N, 5.1. C12H10ClNS requires C, 52.95; H, 4.1; N, 5.1%).

Workup

  1. temperatureat reflux for 4 hours
  2. temperaturecooled
  3. customCrystals which precipitated
  4. customwere removed by filtration
  5. customdried

Sources & evidence

ORD record
ord-cc1b2e34df05478e9cbd04664b54d964
Source dataset
uspto-grants-1983_02
Patent number
US04374992

Reaction notes

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