Dimethylformamide → HCID 58583764, compound

HRID 2249351Notes

Reaction equation

HRID 2249351 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].C[N:16]([CH:18]=O)C>>[CH3:1][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[CH3:1])=[C:4]([C:18]#[N:16])[C:3]=1[C:18]#[N:16]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 87122-ThiocresolHCID 11430Potassium Carbonate

Product 1

HCID 58583764HCID 58583764, compoundYield 42%

Procedure

2-Methylthiophenol (10.60 g, 85.5 mmol), potassium carbonate (11.82 g, 82.0 mmol) and ditosylated dicyanohydroquinone (20.00 g, 42.7 mmol) in DMF (75 mL) were reacted as described above. The mixture was isolated as described above to give a yellow oil. The material was purified by flash column chromatography (eluting 10% ethyl acetate:isohexane) to give the title compound as a yellow solid (8.85 g, 23.8 mmol, 42%). [Found: C, 70.7%; H, 4.6%; N, 7.5%; S, 17.2%; C22H16N2S2 requires C, 70.9%; H, 4.3%; N, 7.5%; S, 17.2%]; MS (EI+) 372 (M+, 100%), 357 (M-CH3, 8), 339 (20).

Workup

  1. customThe mixture was isolated
  2. customto give a yellow oil
  3. customThe material was purified by flash column chromatography (eluting 10% ethyl acetate:isohexane)

Sources & evidence

ORD record
ord-d894e478ca4346788f845d2f4943a11e
Source dataset
uspto-grants-2008_01
Patent number
US07314511B2

Reaction notes

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