Thiophenol → HCID 68275938, compound

HRID 85568Notes

Reaction equation

HRID 85568 reaction equation
[O:1]=[S:2]1(=[O:33])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]2)S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:4][CH2:3]1.C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[O:32]=[S:28]1(=[O:31])[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][NH:10][CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][S:2](=[O:1])(=[O:33])[CH2:7][CH2:6]2)[CH2:26][CH2:27]1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68275931N,N-bis(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

Product 1

HCID 68275938HCID 68275938, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-bis(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.85 g, 1.13 mmol) and thiophenol (0.373 g, 3.39 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.936 g, 6.78 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave a sticky yellow oil (0.381 g, 100% yield). No further purification was performed and the mixture was carried forward to the next step.

Workup

  1. filtrationfiltered
  2. customto remove unwanted solids
  3. concentrationThe crude filtrate was concentrated in vacuo
  4. dissolutionredissolved in methanol
  5. washUndesired materials were eluted from the cartridge with methanol
  6. washthe desired material was released from the resin by elution with 2M ammonia in methanol
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-010c33c3d5664c2daae2708ddec2d82d
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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