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Hexane → 3-Nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridine

HRID 888260
Notes
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Reaction equation

HRID 888260 reaction equation
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[SH:17][C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][CH:21]=[CH:20][N:19]=1.CCCCCC>CN(C=O)C>[N+:24]([C:23]1[C:18]([S:17][CH2:2][CH2:3][S:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:19][CH:20]=[CH:21][CH:22]=1)([O-:26])=[O:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 21702((2-Chloroethyl)thio)benzeneHCID 178526679HCID 178526679, compound

Product 1

HCID 671342393-Nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridineYield 66%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

3.44 g (20.0 mmol) (2-chloroethyl)(phenyl)sulfane and 5.53 g (40.0 mmol) potassium carbonate were added to a solution of 1.56 g (10.0 mmol) 2-mercapto-3-nitropyridine in DMF (30 ml) and heated for 4 h at 60° C. Then the mixture was diluted with EE and washed with brine. The organic phase was separated off, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 9:1) of the residue yielded 1.93 g (6.6 mmol, 66%) 3-nitro-2-(2-phenylsulfanyl-ethylsulfanyl)pyridine.

Workup

  1. additionThen the mixture was diluted with EE
  2. washwashed with brine
  3. customThe organic phase was separated off
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-d3e7cedc03e24bf9af5227f9c7d87216
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08247573B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes