Acetic Acid → 2-((E)-2-Nitro-vinyl)-5-p-tolyloxy-thiophene

HRID 1691024Notes

Reaction equation

C(O)(=O)C.[C:5]1([CH3:19])[CH:10]=[CH:9][C:8]([O:11][C:12]2[S:16][C:15]([CH:17]=O)=[CH:14][CH:13]=2)=[CH:7][CH:6]=1.[N+:20]([CH3:23])([O-:22])=[O:21].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[N+:20](/[CH:23]=[CH:17]/[C:15]1[S:16][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([CH3:19])=[CH:6][CH:7]=2)=[CH:13][CH:14]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To an acetic acid (20.0 mL) solution of 5-p-tolyloxy-thiophene-2-carbaldehyde (2.30 g, 10.5 mmol) described in Manufacturing Example 48-1-2 were added nitromethane (3.20 g, 52.5 mmol) and ammonium acetate (1.62 g, 21.0 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2.5 hours at 100° 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 solvent was evaporated from the filtrate under a reduced pressure to obtain the title compound (2.50 g) as a crude product.

Workup

extractionthe organic layer was extracted with ethyl acetate
washThe organic layer was washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated from the filtrate under a reduced pressure

Sources & evidence

ORD record: ord-66337c5511d840d5b9c8e377ecc8c131
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153662B2

Reaction notes

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