Diisopropyl Ether → 4-(2-Furylmethylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridine

HRID 1275559Notes

Reaction equation

HRID 1275559 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:10][C:11]1[C:16]([CH3:17])=[C:15]([S:18][CH2:19][C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=[CH:13][N:12]=1.[OH-].[Na+].C(OC(C)C)(C)C>>[O:21]1[CH:22]=[CH:23][CH:24]=[C:20]1[CH2:19][S:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([CH2:10][S:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[C:16]=1[CH3:17]

Participants

5

Reactant 4

HCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 224607712-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochlorideHCID 178418431pyridine-4-thiol

Product 1

HCID 221173544-(2-Furylmethylthio)-3-methyl-2-[(4-pyridinylthio)methyl]pyridineYield 89%

Procedure

According to the procedure indicated in Example 1, reaction of 4-mercaptopyridine with 2-chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride and sodium hydroxide solution, subsequent chromatography on silica gel (ethyl acetate/ethanol) and crystallization from diisopropyl ether gives the title compound as a colorless powder; m.p. 126-128° C.; yield 89% of theory.

Sources & evidence

ORD record
ord-d061b64723b6416697c6dcd2e9bb1151
Source dataset
uspto-grants-2000_12
Patent number
US06162809

Reaction notes

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