Nitromethane → 2-(2-Nitro-vinyl)-thiophene

HRID 1843832Notes

Reaction equation

HRID 1843832 reaction equation
C([O-])(=O)C.[Na+].Cl.CN.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.[N+:16]([CH3:19])([O-:18])=[O:17]>CO.CCCCCC.C(OC(=O)C)C>[N+:16]([CH:19]=[CH:14][C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)([O-:18])=[O:17]

Participants

8

Reactant 4

HCID 6375NitromethaneHCID 73642-ThiophenecarboxaldehydeHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochloride

Product 1

HCID 955862-(2-Nitro-vinyl)-thiopheneYield 15%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium acetate (3.6 g, 43.90 mmol) and methylamine hydrochloride (3.01 g, 44.57 mmol) were added to a stirred solution of thiophene-2-carbaldehyde (5 g, 44.64 mmol) in methanol (95.64 mL). This was followed by dropwise addition of nitro methane (108.08 g, 1770.14 mmol) over a period of 5 minutes. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (10% ethylacetate in hexane). The reaction mixture was partitioned between water and DCM. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (5% ethylacetate in hexane) afforded 1 g of the product (15% yield).

Workup

  1. customThe reaction mixture was partitioned between water and DCM
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (5% ethylacetate in hexane)

Sources & evidence

ORD record
ord-1e9a9673209b4157992f98380b8f356d
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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