Acetic Acid → 2-(4-Methyl-benzyl)-5-((E)-2-nitro-vinyl)-thiophene

HRID 1891779Notes

Reaction equation

HRID 1891779 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[S:15][C:14]([CH:16]=O)=[CH:13][CH:12]=2)=[CH:8][CH:7]=1.[N+:20]([CH3:23])([O-:22])=[O:21].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[CH3:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][C:11]2[S:15][C:14](/[CH:16]=[CH:23]/[N+:20]([O-:22])=[O:21])=[CH:13][CH:12]=2)=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 59255325HCID 59255325, compound

Product 1

HCID 592553182-(4-Methyl-benzyl)-5-((E)-2-nitro-vinyl)-thiopheneYield 95.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To an acetic acid (10.0 mL) solution of 5-(4-methyl-benzyl)-thiophene-2-carbaldehyde (1.05 g, 4.85 mmol) described in Manufacturing Example 91-1-2 were added nitromethane (1.48 g, 24.3 mmol) and ammonium acetate (748 mg, 9.70 mmol) under nitrogen atmosphere at room temperature, which was stirred for 4 hours at 110° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.20 g) as a crude product.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-b423b86a2457466fb4a26203e22c8e86
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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