Thiophenol → HCID 45381115, compound

HRID 1615022Notes

Reaction equation

HRID 1615022 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:20][CH2:21][NH:22]S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([C:17](=[O:19])[CH3:18])=[CH:11][CH:10]=3)(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1.C(Cl)(Cl)Cl.CO>CC#N.CO>[NH2:22][CH2:21][CH2:20][N:8]1[C:9]2[CH:10]=[CH:11][C:12]([C:17](=[O:19])[CH3:18])=[CH:13][C:14]=2[C:15]2[C:7]1=[CH:6][CH:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:16]=2

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 21584188Chloroform methanolHCID 67378502HCID 67378502, compound

Product 1

HCID 45381115HCID 45381115, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 52 (4.11 g, 8.58 mmol) was dissolved under reflux in a mixture of CH3CN (150 mL) and methanol (50 mL). Then, Cs2CO3 (8.4 g, 25.78 mmol) was added and at once PhSH (2.6 mL, 25.48 mmol) was poured in. The resulting mixture was refluxed for 2.5 h (TLC monitoring, eluent: chloroform-methanol, 9:1) and evaporated to dryness. Then, water and a solution of HCl were added. As a result, all the solid products were dissolved. The acidic aqueous solution was extracted with ethyl acetate until the latter ceased to become yellow. The aqueous layer was neutralized with a saturated solution of NaHCO3, extracted with a CH2Cl2-MeOH mixture (4:1), and the extract was evaporated. The residue was washed off with MeCN and washed with ether. Yield of 53: 1.25 g (50%) as beige crystals.

Workup

  1. additionwas poured in
  2. customevaporated to dryness
  3. additionThen, water and a solution of HCl were added
  4. dissolutionAs a result, all the solid products were dissolved
  5. extractionThe acidic aqueous solution was extracted with ethyl acetate until the latter
  6. extractionextracted with a CH2Cl2-MeOH mixture (4:1)
  7. customthe extract was evaporated
  8. washThe residue was washed off with MeCN
  9. washwashed with ether

Sources & evidence

ORD record
ord-fe79d1c06e9c43a18ea0e624d818f92e
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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