Thiophenol → HCID 45381115, compound

HRID 514773Notes

Reaction equation

HRID 514773 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-a3f773b3c98c4079ae8f9a765da8bd4f
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

Loading…