Hydrochloric Acid → 4-(3-Mercaptopyridin-4-yl)benzonitrile

HRID 45774

Reaction equation

F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[S-2:16].[Na+].[Na+].Cl>CN(C=O)C>[SH:16][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-(3-fluoropyridin-4-yl)benzonitrile (1.08 g, 5.4 mmol) and sodium sulfide (0.84 g, 10.8 mmol) in DMF (20 mL) was stirred at 130° C. for 0.5 hours. While the reaction was cooled in ice water bath, aqueous HCl (6N, 2.5 mL) was added drop wise with rigorous stirring. The resulting yellow paste was concentrated using rotary evaporation on a water bath (80° C.) to dryness. The resulting yellow solid was extracted with methanol (4×20 mL). The combined extracts were concentrated to dryness to give a yellow solid (1.1 g, 96%).

Workup

concentrationThe resulting yellow paste was concentrated
customevaporation on a water bath (80° C.) to dryness
extractionThe resulting yellow solid was extracted with methanol (4×20 mL)
concentrationThe combined extracts were concentrated to dryness

Sources & evidence

ORD record: ord-dfe61e8317574b2dbb0f1e3faa3d24a2
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541589B2

Linked notes

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