Hydrochloric Acid → HCID 178510369, compound

HRID 714444Notes

Reaction equation

[C:1]1([C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([S:15]C3C=CC=CC=3)[C:8]=2[C:22]#[N:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-2].[Na+].[Na+].Cl>CN(C=O)C>[C:1]1([C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([SH:15])[C:8]=2[C:22]#[N:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

918 mg (2.928 mmol) of 4-phenyl-2-(phenylsulfanyl)pyridine-3,5-dicarbonitrile (Example 36A) were initially charged in 10.7 ml of DMF. 274 mg (3.514 mmol) of sodium sulfide were added, and the reaction solution was then stirred at 80° C. for 3 h, and after 1.5 h another 274 mg (3.514 mmol) of sodium sulfide were added. The mixture was stirred at RT overnight. 5.85 ml of 1N hydrochloric acid were added to the reaction mixture, and the reaction solution was evaporated. 5 ml of tetrahydrofuran were added to the residue, and the precipitate formed was filtered off and discarded. The filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

stirringThe mixture was stirred at RT overnight
customthe reaction solution was evaporated
addition5 ml of tetrahydrofuran were added to the residue
customthe precipitate formed
filtrationwas filtered off
customThe filtrate was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record: ord-40cdd68d8ffe4032baa1c477eec7d64f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187428B2

Reaction notes

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