Nitrogen → 5-Methylsulfanylfuran-2-carboxylic acid ethyl ester

HRID 2064942Notes

Reaction equation

HRID 2064942 reaction equation
N#N.[CH2:3]([O:5][C:6]([C:8]1[O:9][C:10]([N+]([O-])=O)=[CH:11][CH:12]=1)=[O:7])[CH3:4].[CH3:16][S-:17].[Na+].[NH4+].[Cl-]>CS(C)=O>[CH2:3]([O:5][C:6]([C:8]1[O:9][C:10]([S:17][CH3:16])=[CH:11][CH:12]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 70341Ethyl 5-nitro-2-furoateHCID 4378561Sodium methanethiolate

Product 1

HCID 600070005-Methylsulfanylfuran-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 5-nitro-furan-2-carboxylic acid ethyl ester (5.00 g, 27.01 mmol) in DMSO (34.5 mL) was treated at rt with sodium methanethiolate (2.05 g 27.82 mmol). The mixture was then stirred at 100° C. overnight, cooled down to rt and treated with sat. aq. NH4Cl (250 mL). The aqueous layer was extracted with EA (3×100 mL). The combined org. extracts were washed with sat. aq. NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound. TLC: rf (70:30 hept-EA)=0.52. LC-MS-conditions 02: tR=0.96 min; [M+AcCN+H]+=228.23.

Workup

  1. temperaturecooled down to rt
  2. extractionThe aqueous layer was extracted with EA (3×100 mL)
  3. washextracts were washed with sat. aq. NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (70:30 hept-EA)

Sources & evidence

ORD record
ord-388880270fc4471c9980812d4e7fe42b
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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