4-Methoxybenzenethiol → HCID 57585082, compound

HRID 2077498Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Cl)[N:14]=1>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([S:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Methoxythiophenol (Aldrich, St. Louis, Mo., Cat. No. 109525; 0.91 mL, 7.4 mmol) was dissolved in DMF (10 mL) and chilled to 0° C. in an ice bath. NaH (0.227 g, 9.5 mmol) was added slowly and the mixture was allowed to stir under an inert atmosphere. After 1 hour, 2,6-dichloropyridine (1.000 g, 6.8 mmol) was added to the mixture and the ice bath was removed. The resulting mixture was allowed to stir under inert atmosphere overnight. The mixture was quenched with 1N NaOH and diluted with DCM. The aqueous layer was extracted with 4:1 DCM/MeOH three times, and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (1-30% DCM/hexanes) to give 2-chloro-6-(4-methoxyphenylthio) pyridine (0.950 g, 56% yield) as a yellow oil. MS (ESI pos. ion) m/z: 252 (MH+). Calculated exact mass for Cl2H10ClNOS: 251.

Workup

customthe ice bath was removed
stirringto stir under inert atmosphere overnight
customThe mixture was quenched with 1N NaOH
additiondiluted with DCM
extractionThe aqueous layer was extracted with 4:1 DCM/MeOH three times
dry with materialthe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by silica gel chromatography (1-30% DCM/hexanes)

Sources & evidence

ORD record: ord-3e95f83817a14052874dce1720fb41c7
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928140B2

Reaction notes

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