Thiophenol → HCID 66938707, compound

HRID 1893582Notes

Reaction equation

HRID 1893582 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([CH3:50])[C:11](=[O:49])[CH2:12][N:13]([C:36]2[CH:41]=[C:40]([C:42]3[N:46]=[C:45]([CH3:47])[O:44][N:43]=3)[CH:39]=[CH:38][C:37]=2[CH3:48])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][N:20]([CH:33]([CH3:35])[CH3:34])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)=[O:16])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.ClCCl>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([N:10]([CH3:50])[C:11](=[O:49])[CH2:12][N:13]([C:36]2[CH:41]=[C:40]([C:42]3[N:46]=[C:45]([CH3:47])[O:44][N:43]=3)[CH:39]=[CH:38][C:37]=2[CH3:48])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][NH:20][CH:33]([CH3:35])[CH3:34])=[O:16])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 68159452HCID 68159452, compound

Product 1

HCID 66938707HCID 66938707, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (260 mg, 0.365 mmol) obtained in step D was dissolved in acetonitrile (3 ml). Then, benzenethiol (0.057 ml, 0.547 mmol) and cesium carbonate (594 mg, 1.82 mmol) were added, and the mixture was stirred at room temperature for 10 hr. The reaction mixture was diluted with dichloromethane, and the organic layer was washed with diluted aqueous sodium hydroxide solution, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (NH silica gel use, methanol-dichloromethane) to give the title compound (161 mg, yield 84%) as a pale-yellow amorphous solid. This was directly used for the next step.

Workup

  1. washthe organic layer was washed with diluted aqueous sodium hydroxide solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe obtained oil was purified by silica gel column chromatography (NH silica gel use, methanol-dichloromethane)

Sources & evidence

ORD record
ord-d015302b86814d2e83d466f845d8c0d2
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

Loading…