Bromide ion → 2-{[(2-Methylfuran-3-yl)sulfanyl]methyl}pyridine

HRID 1287937Notes

Reaction equation

HRID 1287937 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[SH:7].[Br-].[Cl-].Cl.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17]Cl.C[O-].[Na+]>CO.C(O)(C)C.C(O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][S:7][C:6]1[CH:5]=[CH:4][O:3][C:2]=1[CH3:1]

Participants

9

Reactant 5

HCID 259Bromide ionHCID 312ChlorideHCID 23392Picolyl chloride hydrochlorideHCID 342862-Methyl-3-furanthiol2×HCID 10942334Sodium Methoxide

Product 1

HCID 215030882-{[(2-Methylfuran-3-yl)sulfanyl]methyl}pyridine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 3776IsopropanolSolvent

Procedure

The 3-furyl sulfides of our invention can also be prepared by reacting 3-furan thiols, e.g. 2-methyl-3-furan thiol with an α-picolyl halide (2-pyridyl-methyl halide) (e.g. a bromide or chloride); (i) in the presence of a base such as an alkali metal alkoxide (e.g., sodium methoxide); (ii) at a temperature in the range of 15°-65° C; and (iii) in a suitable solvent, e.g., an anhydrous lower alkanol such as anhydrous methanol, ethanol or isopropanol. Thus, for example, α-picolyl chloride hydrochloride, when reacted with 2-methyl-3-furan thiol in anhydrous methanol in the presence of sodium methoxide at a temperature of 24° C will yield (2-methyl-3-furyl) (2-pyridylmethyl) sulfide.

Workup

  1. customin the range of 15°-65° C

Sources & evidence

ORD record
ord-cd9c8c5db62644c09468a83c03a51524
Source dataset
uspto-grants-1976_10
Patent number
US03985908

Reaction notes

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