Water → HCID 58583762, compound

HRID 2249352Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].O.C[N:17]([CH:19]=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:4]([C:19]#[N:17])[C:3]=1[C:19]#[N:17]

Participants

Reactant 4

HCID 962Water

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 80599o-Chlorothiophenol

Product 1

HCID 58583762HCID 58583762, compound

Procedure

2-Chlorothiophenol (12.50 g, 86.5 mmol), potassium carbonate (11.94 g, 86.5 mmol) and ditosylated dicyanohydroquinone (20.36 g, 43.5 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 (eluting 30% ethyl acetate:isohexane) to give the title compound as a yellow solid (5.53 g, 13.4 mmol, 31%) [Found: C, 58.1%; H, 2.7%; N, 6.9%; S, 15.4%; Cl 16.6%; C20H10N2S2Cl2 requires C, 58.1%; H, 2.4%; N, 6.8%; S, 15.5%; Cl 17.2%]; MS (EI+) 412 (M+, 100%)

Workup

filtrationthen filtered
customThe filter cake was purified by flash column chromatography (eluting 30% ethyl acetate:isohexane)

Sources & evidence

ORD record: ord-8f79230881e7487e9c02a8a669f756be
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314511B2

Reaction notes

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