Imidazole → 4-[3-(1-Imidazolyl)propylthio]-3-methyl-2-[(4-pyridinylthio)methyl]pyridin

HRID 1275563Notes

Reaction equation

HRID 1275563 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[C:7]=1[CH3:20].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[K+].[K+]>>[N:21]1([CH2:2][CH2:3][CH2:4][S:5][C:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[C:7]=2[CH3:20])[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 221173024-(3-Chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine

Product 1

HCID 221173154-[3-(1-Imidazolyl)propylthio]-3-methyl-2-[(4-pyridinylthio)methyl]pyridinYield 32%

Procedure

According to the procedure indicated in Example 7, reaction of 4-(3-chloropropylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine with imidazole (2.0 equivalents) and potassium carbonate and subsequent chromatography on silica gel (dichloromethane/acetone/NH3 aq) gives, after crystallization from diisopropyl ether, the title compound; m.p. 117-119° C.; yield 32% of theory.

Workup

  1. customgives
  2. customafter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-b1ae5573509b496e9096212d216b6b9a
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

Loading…