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

HRID 640346Notes

Reaction equation

HRID 640346 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-e08139cc3fae4de08106a9c05c1c2b54
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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