Thiophenol → HCID 131735283, compound

HRID 627151Notes

Reaction equation

HRID 627151 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[C:23]([CH2:24][O:25][CH3:26])=[CH:22][CH:21]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[NH:20][CH2:19]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][C@H:18]1[C:23]([CH2:24][O:25][CH3:26])=[CH:22][CH:21]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 131735284HCID 131735284, compound

Product 1

HCID 131735283HCID 131735283, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of Intermediate 120 (5 g, 9.47 mmol) and K2CO3 (7.86 g, 56.85 mmol) in acetonitrile (100 mL), PhSH (3.90 mL, 37.90 mmol) was added. The reaction was stirred at rt overnight. It was filtered and concentrated, then diluted with DCM and filtered through disposal filter. The filtrate was concentrated and purified by silica gel column (0-100% Hex/EA, 80 g ISCO) to afford the title compound (2.04 g, 63%) as an oil.

Workup

  1. additionwas added
  2. filtrationIt was filtered
  3. concentrationconcentrated
  4. additiondiluted with DCM
  5. filtrationfiltered through disposal
  6. filtrationfilter
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column (0-100% Hex/EA, 80 g ISCO)

Sources & evidence

ORD record
ord-ba40336d803a4588b232635692069dff
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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