Water → HCID 58583766, compound

HRID 2249350Notes

Reaction equation

[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].O.C[N:16]([CH:18]=O)C>>[C:1]1([S:7][C:4]2[CH:5]=[CH:6][C:1]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:2]([C:18]#[N:16])[C:3]=2[C:18]#[N:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 4

HCID 962Water

HCID 6228Dimethylformamide

HCID 7969Thiophenol

HCID 11430Potassium Carbonate

Product 1

HCID 58583766HCID 58583766, compoundYield 52%

Procedure

Thiophenol (11.75 g, 107 mmol), potassium carbonate (14.74 g, 107 mmol) and ditosylated dicyanohydroquinone (25.00 g, 53.0 mmol) in DMF (80 mL) were reacted as described above. Water (100 mL) was added and the mixture stirred for 1 hour then filtered. The filter cake was purified by flash column chromatography (gradient elution 10%-30% ethyl acetate:isohexane) to give the title compound as a yellow solid (5.53 g, 16.1 mmol, 52%). [Found: C, 69.6%; H, 3.5%; N, 8.2%; S, 18.3%; C20H12N2S2 requires C, 69.8%; H, 3.5%; N, 8.1%; S, 18.6%]; MS (EI+) 344 (M+, 100%).

Workup

filtrationthen filtered
customThe filter cake was purified by flash column chromatography (gradient elution 10%-30% ethyl acetate:isohexane)

Sources & evidence

ORD record: ord-15dbeaa659714f6b84db64de5621342e
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314511B2

Reaction notes

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